A few weeks ago, I wrote a post that asked whether a female boss can manage a chauvinist. I’ve struggled with this issue for many years, and from your replies it’s clear that other women have endured similar experiences.

More than 300 people wrote comments, and hundreds more contacted me through Twitter, LinkedIn and email. I had asked for feedback in the article but was amazed by the level of interest. From helpful advice to shared dismay to fierce criticism (of me), there were lots of opinions on this topic.

I have now read every comment and email, and I have learned a lot from your thoughts. And while I can’t write to everyone individually, I wanted to thank you and share some of what I took from the messages.

First, your answer to my question, “Can a female boss successfully manage a chauvinist?” was a resounding no. In the post, I told the story of a male I’d interviewed who displayed signs of chauvinism but was otherwise a great candidate. When I wrote the post, my business partner and I were considering whether we should give the guy a go. I was worried that he wouldn’t respect me but conscious that we needed to fill the role quickly.

Almost every person who responded to the article implored me not to hire this person. One of my favourite comments came from a relationship expert who said, “The reasons for divorce are almost always apparent on the first date.” And the same is true in recruitment. If he showed signs of disrespect in the interview, that would most likely lead to a painful breakup in the future.

Others reminded me of the close working relationships we must develop with employees. Posse is a small but ambitious tech start-up. We’re a tight, passionate team that works round the clock to make our company a success. There are tough times when we need to pull together, and great highs when we celebrate together. We’re a family, and this only works because of a foundation of mutual respect. As the chief executive, my relationship with all members of the team is vital. If they don’t respect me, they won’t buy into my vision — and I won’t be able to inspire them to perform.

Many of you will be pleased to hear that we decided not to hire this particular candidate. Initially, I thought I’d be able to change his perspective. Surely after we started working together he’d see how awesome I was and respect me. One of the emails I received told a story of how, as leader of a company, this person thought she could change one of her colleagues, but after months of frustration and stress gave up. She reminded me that it can be difficult to change ourselves and all but impossible to change others.

Another lesson from your feedback was for me to take responsibility for my own leadership style. In the post, I described the ways I’d attempted to manage an engineer who didn’t listen to me. First I tried to be tough and aggressive. Then I brought in others to support my ideas. Finally I turned to acting like a “hopeless girl” in order to elicit his sympathy and help. One commenter said she couldn’t believe how I had “wound myself up into a pretzel” to deal with the situation.

Reading the post again, I couldn’t believe it either. Many of you urged me to be confident in my own management style, more direct: “It’s your business, and if someone isn’t respecting you then let them go. Don’t try to lead from the shadows.”

You’re right! I wonder if women find this approach more challenging than men do – I know I do. I want people to be happy and I adjust myself to make relationships work. It takes confidence to hold your ground, but I suspect that’s the only way to establish authority.

Thank you for all of your stories – I wish I could share every one of them. I especially enjoyed reading emails from women around the world, all of whom had experienced chauvinism in their workplaces. Many had overcome much tougher situations than my own.

One woman wrote about her experience as a senior member of the United States Air Force whose male subordinates wouldn’t accept orders from her. She told of her frustration when they refused to return phone calls or answer emails and would respond only to a man. She didn’t have a magic solution but wrote about how she’d battled through, up the ranks. It’s women like this who teach men that women can lead powerfully and become role models.

A woman from the Middle East wrote a heartfelt email about her experiences establishing a business in the construction industry. In my post, I described how a male tried to shake my hand in the dominant position – with his hand faced down. She described how, where she lives, most men refuse ever to shake the hand of a woman – even if she’s the boss or a client. This reminded me how far we’ve come here and how much harder it may be for women entrepreneurs in other cultures.

In my post, I wrote about a senior job candidate who checked out an attractive waitress mid interview and gestured to my male colleague to do the same. Several of you wrote that you were disappointed that I didn’t comment on this unacceptable behaviour at the time, and I think you were right about this too. We should call out sexism when we see it and raise awareness of these issues for the next generation.

I accept that by being direct and confident in my leadership style and by not associating with idiots, I can overcome many of these challenges. But I had to write a New York Times post in my mid-30s to fully understand this.

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I don’t really enjoy working with lawyers, yet every time I start a new relationship with one I’m filled with hope. They seem impressive in their fancy suits and expensive offices. They woo me with flattery and nice cups of tea and biscuits. I find myself thinking: These guys are cool. I’m going to work with them forever.

I brief them on what we’re looking to achieve. We meet another couple of times, we agree to move forward and then I ask for the cost estimate. But in seemingly no time at all, it turns out I’ve run up a bill I wasn’t expecting and can’t afford to pay.

When I’m looking for a lawyer, it’s usually because there’s a job I need to get done. By the time I’ve had a couple of getting-to-know-you meetings and I’m ready to engage the lawyer’s services, a few weeks have passed. The not-so-urgent job has become urgent and so the lawyer gets started.

I’ve learned to ask for a quote and a cost agreement, but in an effort to move quickly the lawyers often move ahead before I realize it. For some reason they’re much quicker at getting started with work than they are at costing out the work I need done. And before I have a chance to mention that my company is a poor start-up, I’ve been sent a bill for $20,000.

But I’m learning. I think that the trick is to be upfront about our company’s financial position: We’re a start-up! We can’t afford to pay big, unexpected bills. We must agree in writing on a maximum quote for any piece of work; any addition to the quote must be approved by me, also in writing. Lawyers who start work before a quote is agreed upon do so at their own risk.

I tried this approach recently. We agreed in writing to a maximum charge, and we agreed that any additions to the bill must be approved in advance. When the invoice arrived, for far more than the quote, I had an email trail. The lawyers grumbled about the amount of extra time they had spent, but there was no real argument. They reissued the invoice for the original quote.

Sometimes we start-ups need to use expensive lawyers with good reputations. If we’re negotiating with large investors or corporations, they expect to deal with firms they know. These big firms want to work with us — not because we pay big fees but because there’s a chance we’ll be able to do so in the future. If you find yourself in this position, where you need to engage one of these firms, here are some of the things I’ve learned to be especially clear about. Specifically, I’m not paying for:

1. Sales meetings

Introductory meetings where the lawyers are selling their services should not be charged. And we need to know precisely when we leave the courtship stage.

2. Reading irrelevant documents

Often a new lawyer will ask for all company documents to be sent through — even if they’re not at all relevant to the job at hand. Recently, I was asked to send through a bunch of documents ahead of an introductory meeting so the lawyer could scope and cost out our job. I questioned why the documents were required and was told they were needed as background. When I received a bill for $3,000 for “reading” the documents, I disputed it — and won.

3. Briefing internal colleagues

Once, I was working with a partner at a top firm in the city. Attempting to keep costs down, I was careful to keep my meetings with the partner short. This partner was the only lawyer I dealt with at the firm, but when I received the bill, I’d been charged for tens of hours of work by someone else I’d never met. I was charged for one hour of the partner’s time for each meeting and then another hour for the partner to brief a colleague and yet another hour for the equally expensive colleague to receive the briefing. I disputed this on the grounds that if someone else was going to do the work, I shouldn’t have to pay for this new person to be briefed internally. I later heard that other chief executives negotiate a no-charge-for-internal-briefing clause, and I now specify upfront that I won’t be paying for this.

4. Making things unnecessarily complicated

Sometimes legal deals and documents can be complicated and need a lot of tweaking, negotiating and explaining. But often they’re quite simple. Recently we undertook a friendly transaction with another business. Our lawyer drew up the contract and we had to show it to the other party’s lawyer for sign-off. It was a friendly, straightforward deal, and everyone involved just wanted the other lawyer to say it was O.K. or flag any issues. Instead, the lawyer took two weeks and sent back a document that was almost completely reworded but said exactly the same thing. Of course, we also got a hefty legal bill.

We then had to show the changes to the original lawyer, who charged again to review it and changed some of the wording back because he thought his version was clearer. Both agreed the changes were substantially meaningless but both seemed to think they had to show they were doing a good job by suggesting improvements. All we wanted was to move quickly at low cost, which was the opposite of what we got.

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Every week, I get invited to another “must attend” business event sure to be full of important people who could affect my business. I know I should go, but it’s a chore. All too often, I end up standing in a corner clinging to the one person I know, feeling guilty that I’m not taking advantage of the situation. Recently, I attended a business women’s networking breakfast, held in a large warehouse near the waterfront. I marched through the door and collected my name tag to confront a roomful of 1,200 colorfully dressed, high-energy women chattering. Everyone appeared to be having a great time, making connections. What next? Do I know anyone here? If I stand all alone will people think I’m weird? I feel my chest tighten.

I suspect that many of us struggle at these events, but few admit it. Everyone slaps on a smile and wanders around the room shaking hands, laughing and exchanging business cards. Inside, some of us feel awkward, loitering at the edge of conversations, unsure whether to enter the group or slip away. That’s me. If you follow my posts, this may surprise you. I’ve built a powerful network and convinced leaders from Google, eBay, Twitter and Facebook to support my start-up, so you might suppose that I’m an expert schmoozer. Truth is, as an introvert, I’ve struggled with networking for years. I’d much rather be home reading a book.

But I recognize the importance of this type of activity, so I stick to it — primarily because a few chance encounters at events have led to relationships that have made all the difference in my business. I have to accept that networking doesn’t come naturally to me, and that’s hard. I’m a perfectionist. I like to be good at things. So I’ve developed techniques to help me form relationships and improve, even enjoy, the networking process. If you, too, struggle with networking, here are a few ideas that may help.

1. Have short conversations with lots of people. Follow up later

I find it difficult to form deep connections at events. Instead, I try to have short conversations with as many people as possible, making sure I have their contact information so I can follow up later. If I see someone I want to talk to, I politely dart in and say, “I’m sorry to interrupt, but such and such suggested we meet. I have to run in a minute and just wanted to get your business card so I can follow up later.” It’s quite hard for people to say no to this. And then after the event, I reach out and set up lunch or coffee. That’s an environment in which I’m much more comfortable.

2. Focus on what you’re good at

Although I find large informal groups a challenge, I know that I perform well in formal presentation settings or one-on-one conversations. Instead of worrying about my inability to charm at large-group events, I focus my on my more natural ability to engage people one-on-one and to speak publicly. If you can kill it in a one-on-one presentation, that’s all you need to do to build a network.

3. It’s about forming a few close relationships

Some people have hundreds or even thousands of people in their network. Other than on social networks where I don’t know most of the people to whom I’m supposedly connected, I’d say my close business network includes about 15 people, but they are special. Every year, I meet between one and three people who are magic. It’s never about what this person can do for me; it’s a realization that I’ve encountered someone I can learn from. Almost all of the good things that have come to me have come from one of these 15 people.

We introverts have different strengths. For example, check out this great TED talk by Susan Cain on “The Power of Introverts.” I spent years thinking that I should be different — louder, funnier, more extroverted. Now I recognize the need to be grateful for the talents that I do have.

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A few weeks ago, my business partner and I interviewed a candidate for a senior communications role at Posse. We met at a coffee shop and he seemed perfect: charming, smart and passionate about our business. He’d been successful in similar roles, and he came to the interview prepared with suggestions relevant to our strategy. I was impressed. But a couple of things bugged me. Ten minutes into the conversation his eyes swung behind our table and toward the counter. I turned to see what had caught his attention: an attractive waitress. I looked at him quizzically — he knew I’d noticed what he was staring at but he didn’t seem to care. He smiled and gestured for my male business partner to check her out.

I couldn’t help but notice for the rest of the interview that whenever he spoke about anything serious he focused his attention on my male partner. He answered my questions well, but often with a flirtatious smile before shifting his attention back to the male in the room — the person he obviously assumed was the boss. At the end of the meeting he held his hand out to shake mine in the dominant position — palm facing down. By now I was fuming — I grabbed his hand from the side and we had an uncomfortable moment.

When my business partner and I discussed the interview afterward, we both had the same concerns. He also felt that his behavior toward me in particular, and possibly toward women in general, was poor. But we also agreed that in every other respect, this guy was ideal for the role, and we had been searching for a strong candidate for quite a while. We considered that one of his assignments, if hired, would be to relate Posse to prospective corporate partners, which meant his flirtatious nature might come in handy. Some of the best business communicators apply their skill and charm to their advantage. Still, that left us with some big questions. Could he respect me as a founder and leader of the business? Can a female boss successfully manage a chauvinist?

Working in the technology sector means that just about everyone surrounding me is male. I’ve learned to deal with loneliness, lack of emotional support and prospective investors who sometimes make inappropriate comments. But what really gets me is knowing that it may be fundamentally impossible to lead some people who cannot respect me because I am a woman. This bothers me because I want to be a great C.E.O. I’m not suggesting all males are like this. It’s unusual for candidates to demonstrate disrespect toward women in an interview with me. Once I’ve hired them and struggle to connect, I often question what has gone wrong. Do I have a poor leadership style, or are they not listening because they think I’m inferior?

A few years ago in another business I had a senior engineer who was brilliant but a chauvinist through and through. I tried every approach I could think of to win his respect. I started by acting like a man myself — aggressive, tough and demanding. It didn’t work. He wasn’t used to a woman acting like that and was offended. Worse still, he sniggered to colleagues and ignored me altogether. Then I brought in other people to support my positions. We had some high-profile investors and board members, and when I wanted to convince him of something I would Skype one of them into the conversation so that the idea would sound as if it were coming from someone he respected. This often succeeded in helping me win an argument but deflected the long-term problem.

Finally, I tried to charm my way into his heart. I played the “girl” role — unsure of myself and in need of his help. I acted as if somehow I had managed to put this whole company together by luck. I joked about how I was running a tech company but didn’t know anything about how it actually worked. This was a lie — I had studied physics, and I’ve spent a lot of time learning about code and frameworks for development. The approach failed anyway. I was able to get him to like me but it killed any authority I might still have had.

Eventually, I had to let this engineer go. It was hard because he was the office superstar — the smart guy everyone respected. But he wouldn’t take my product road map or my development schedule seriously because he thought I didn’t know what I was talking about. I learned that there was no way we could work together. Those of you who follow my posts know that I generally write about issues I’ve faced at Posse once I’ve figured out an answer. Then I share what I’ve learned and my tips for addressing the problem.

This time, I haven’t figured out a satisfactory answer, and I’d like to hear from you. Are you a female leader who has faced similar challenges with your male employees? Have you worked out how to harness the confidence of chauvinistic characters and have them succeed in your business? If you’re a male who has experienced working with a strong female boss — what was it that won your respect? If I hire the candidate I mentioned at the start of this post, can I manage him successfully?

Please write your opinions and experiences in the comments. I’d love to hear your thoughts.

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A lot of people want to tell me how to run Posse.

At the moment we’re deciding whether to raise a large capital round and go for growth or keep things tight and focused. Both approaches have merit, and I respect all who have offered their guidance. But people are passionate about their opinions, and that can prove confusing. When I started my business four years ago, I was hungry for advice. I’d never worked in technology and had no experience raising capital or building a product. I cast my net as far as I could and sought help from people who seemed to know what they were doing.

Finding support was easy. Everyone I approached liked my idea; many wanted to be involved. I created an advisory board and handed out shares as if they were candy. I surrounded myself with impressive names, and they all had friends they wanted me to meet. Before I knew it, I had 50 shareholders, and we were all on a sugar high. Everyone had ideas and opinions, and they all wanted to meet with me. Many gave me books to read and research to do. I sipped coffee after coffee and read deep into the night. I wanted to appear grateful for the support, so I reported back on how I’d benefited from the advice and emailed notes on what I’d learned from each book.

All of the advice appeared valid, but much was contradictory. I didn’t want to give offense by ignoring well-intentioned suggestions, and I burned up time holding meetings and keeping up with my reading list. I couldn’t make decisions and had no time to focus on getting work done. But I was confident that my roster of advisers would pay off by impressing potential investors when I went to raise my first round of capital. Surely they would boost my credibility.

Not exactly. During pitches, every time the adviser section of my deck came up, I got the same response: “I’m impressed you got X and Y involved. Have they invested?” Well, no, they had not, which led to a follow-up question: “If experts in the field hadn’t committed to investing despite knowing all of the company’s details, why should we?” Once I realized that these big name advisers who hadn’t invested were having a negative impact on my ability to raise capital, I removed all references to noninvestors from my presentation.

Now I’m four years in, and I still crave advice. I think being a sole founder increases my need for reassurance that I’m on the right track. I always find that having a wide range of discussions, as we often do during fund-raising, helps me refine my strategy. But I’ve also found that too much advice can be a distraction and that advisers who want equity but aren’t willing to back the company are not always the best people to have involved. Now the company is moving on to the next phase of growth. We’ve been a start-up valued at less than $10 million with good prospects but with a small team and with very little revenue. As we start to become a serious business with significant revenue, I’m beginning to move in a different world, one where I need new advice.

I’m also at the next phase in my own growth. I used to see myself as inexperienced and in need of help. Now I make my own judgments rather than deferring to people I see as experts. I still ask people I respect for their opinions and ideas, but I’ve developed a strong sense of whom to trust. I’ve learned a big difference exists between people who enjoy giving advice and those who really care about me and the business. There’s also a big difference between people who think they know how to build a company like ours and those who have actually done it.

I can think of four people who have helped me at Posse and without whom we would have failed. But the new phase we are entering requires a new group of advisers. Here is some of what I’m looking for:

1. Previous success in similar fields

Some of the people I enlisted to my early advisory board sounded impressive. They’d held high-level positions at big corporate companies. When we suffered some early start-up bumps, though, they were unprepared. Their knowledge of how a start-up should grow was based on watching “The Social Network.” When we didn’t hit it big straight out the gate, they became concerned. I learned to look for people who had built a similar company from the ground up.

2. Focus on the granular

Many people who want to give me advice start with a discussion about the potential size of the exit and how quickly we’ll be able to get there. This always creates distractions such as attending to the setting up of complicated corporate structures to minimize future tax or setting up big sales deals ahead of building a product. I’ve found that the best advisers are the ones who drill me on what we have to achieve in the next three months. They’re interested in the granular metrics of the business, how we can improve them and how we can create replicable processes.

Good start-ups are rarely short of willing advisers. Maybe these people are looking for involvement in something that looks like fun; maybe they seek a slice of a big exit. But I’ve developed a keen radar for time wasters. I spend as much time as possible getting to know someone before inviting them to become involved. I do thorough reference checks and never give away shares in the company without a vesting period.

When I do find someone who’s right, I recognize that the relationship has value. Such people are usually in high demand; they’re giving up other opportunities to take a risk and help me. Time is their most valuable asset, so I make sure I’m prepared for meetings and I check in regularly to make sure that they’re happy with our progress and that they enjoy being involved.

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I spent a recent night consoling an associate who had fallen out with her best friend. They tried to start a business together, and she quit her high-paying job to do it. Three months in, the friend had yet to commit full-time and wasn’t pulling her weight. They couldn’t agree on how to split either the tasks or the ownership stakes. Tension built and eventually exploded, and the business died before it was born. Their 15-year friendship was over.

I started my business, Posse, with my best friend, too. We’d worked together as colleagues for eight years and respected each other’s strengths. I spoke at his wedding and trusted him completely, and we were, indeed, close. He was the first person I called when I came up with the concept, and he appeared enthusiastic. But a few months in, he announced that he was starting another company, one that wouldn’t interfere with Posse. Soon after, he disappeared. Suddenly, I was running Posse full-time and solo. He did keep his founder shares, but we no longer speak. I lost a significant chunk of the business and my best friend (which was worse).

These situations arise all the time. Sometimes they make news when the friendship that is breaking up was behind a prominent company. The results can be disastrous for the business and heartbreaking for the individuals. Of all the dramas that entrepreneurs discuss with one another over drinks — often several drinks — I find that the merging of personal relationships with business seems to cause the most pain.

Melanie Perkins and Cliff Obrecht at the offices of their company Canva. Picture: Jeremy Piper.

People start with the best intentions. Most partners appreciate one another and have high regard for one another’s ability and integrity. It’s only natural to want to build something with a trusted friend, someone whose company is welcome. And yet, so often, it all falls apart. Within my group of friends are three couples who started technology companies together. Two divorced within the first four years but still run successful businesses as a team — not without some pain, I imagine.

The other couple grew stronger. Melanie Perkins and Cliff Obrecht have been running companies together for the last seven years. Two years ago they founded an online graphic design company, Canva, that is going through a growth explosion, with more than 750,000 users in the first year. They appear to have the perfect partnership — they complement each other’s strengths and drive the business forward in tandem. In an effort to understand why Mel and Cliff have thrived as partners, while so many others, myself included, have struggled, I asked them to share their secrets. Here’s Mel’s advice:

1. Keep the dream alive

Mel says she and Cliff have always been clear about what their vision is for the business. Every day they talk about what Canva will look like in five to 10 years. “When you know what you both want to build,” she said, “it makes every little decision easier. They’re all steps toward a shared dream.”

2. Have unstructured conversations

“We do lots of walking where we’re free to have crazy conversations and brainstorm ideas,” she said, adding that in business, it’s easy to have rigid boardroom-type discussions in which everyone is afraid to speak openly for fear of side-tracking the meeting.

3. Don’t keep battle scars

Once a decision is made, it becomes a team decision. There is always discussion, but what matters is working toward the shared vision. “We always focus on the best outcome for the business,” she said. “Once something is agreed, the process behind the decision isn’t mentioned again.”

4. Build trust over time

Mel describes how, during the first few years of working together, they were both involved in everything. Over time, as the company has grown, they’ve developed trust and chosen to focus on different areas. “We’re in business together because we believe in each other’s skills,” she said. “It’s great that we each get to play to our strengths, because it means we can cover a lot of ground.”

5. Have the same expectations of each other

“Both of us have an extremely high work ethic,” Mel said. “We’re focused on the business 24/7, and a common expectation of ourselves and each other provides the foundation that makes everything else possible.” In my experience, it’s very hard to have dual roles in a relationship. But I’m incredibly jealous of those who can pull it off. With your best friend by your side, the journey through the highs and lows of business would be magical.

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This is the story of a trap into which I’ve fallen twice at Posse. Investors often set the trap unknowingly – no harm is intended – while they are figuring out whether they would like to invest. Both times this happened I felt heartbroken and exhausted, with my business in turmoil. We were lucky to survive.

It all starts so well. You meet venture capitalists and deliver a knockout pitch. They love it, you exchange business cards and they set out the next steps. First, you have to meet a few other people from the firm. They are busy so it can take a few weeks to secure the appointments, but they are genuinely interested and they ensure that you are seen as quickly as possible. You meet again for lunch, then dinner, then drinks. You become friends.

You discuss the wondrous opportunities for your business and the ways in which they can help you reach those opportunities. Watch out: You’ve started to fall in love. You discuss generalities about the deal terms, big stuff like the valuation and how much they’ll invest (a lot). And of course, they will want a seat on the board. You are excited; this will transform your world. In no time, you are planning how you will spend the money, looking at new office space and thinking about recruiting new team members.

One of the senior partners you needed to meet with was traveling, so you wait six weeks for the meeting. It is promising, too; he wasn’t as excited as the junior guys, but he likes them to be autonomous and allows them to pick their own deals. The senior partner suggests you meet a friend of his who runs a big company that, he says, would make a great partner for your business. It sounds helpful, but you know he really wants to know what his friend thinks of you. The company is based in Chicago; you have to travel and the meeting takes two more weeks to set up. All goes well, and after a week you hear the firm wants to move forward with your deal.

Next comes due diligence. This starts with a long list of requests and a promise that, once all the information is together, this will not drag on. They guarantee you will receive the term sheet within two weeks, so you pull in your team and work late — very late — to assemble the material. It may include questions like: Who owns all these shares on the capitalization table? Is there anyone here without an employment contract? Why did you model revenue this way? Will you really need all those engineers?

You answer all of the questions diligently, repeatedly rework your financial model, and either make changes to your contracts or write new ones. More than a month passes. You have spent money you do not have getting help with contracts, accounts and a revenue model to satisfy the investors. You have answered almost every tricky question that could be asked about your business plan, your competition and the market. Everyone seems happy and the firm assures you that due diligence is almost complete. The term sheet is only days away. Four months have past since you first met. There is one more thing — a meeting, a problem, a question, something that is going to take more time. Finally, you start talking about investment terms. And then something happens. It could be any number of things, but it is a knockout blow that kills your deal.

The first time this happened to me, I had negotiated for five months with a big name corporate brand. The company had proposed investing $3 million dollars, and the association would have catapulted Posse’s profile to the stars. I liked the executives leading the deal and could not wait to build the business with them. They assured me that they could move quickly and that they would reach a decision within a month. But the months dragged on and more people became involved, asking more questions. I was not even worried; I was so sure we would close the deal. After all, they would not invest so much of their company’s time if they were not serious, would they? But when the terms came back, they killed the deal; they were nothing like the proposal we had discussed when we first met. The company would invest, but it came up with a valuation of less than half what we expected. I might have accepted anyway, but our board refused.

Last year, I spent six months attending to the whims of a group of angel investors from New York. It took three months to complete a series of qualification presentations, after which they selected a cast of a dozen members to perform the due diligence. I answered their questions, reworked financial models and met every relevant person full time. They said they would invest more than a million dollars, and the process required only four to six weeks. Then they told me they could not invest nearly as much as they had thought. The exercise had been a gigantic waste of time, distracting me from talking to other, serious investors.

I remember venting my frustration during one of these drawn out episodes with one of my mentors. He said, “Never start due diligence until you’ve agreed on a term sheet.” With hindsight, it seems so obvious. If I had refused to do any work until a term sheet had been worked out up front, then I would not have spent months and tens of thousands of dollars pleasing investors who were not serious, did not have the money or whose deal expectations were vastly different from ours.

The problem is, refusing to do any work until a term sheet is signed sounds great but is hard to do. When you first meet, you are excited and the investor promises that the process will take only a few weeks. You can afford to invest a few weeks. Even as time drags on, everything appears to be proceeding, and you are certain the deal will close. As time drags on, costs pile up and cash reserves dwindle. You realize that, with so much time invested, you cannot afford to start the process again.

I will never get stuck in this situation again. I will never let an investor seduce me into believing that a term sheet is around the corner while I put time and money into meetings and answering thousands of questions. I will ensure that a term sheet is agreed upon up front and then start the due diligence process. If the V.C.s find something they do not like during due diligence, they can always back out of the deal, but at least I will have established that there is a deal to be done. Even though I know their firm is big and my company is small, I will do this because I know that time and energy are my biggest assets.

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Recruiting the right team member is always difficult. I start off knowing that I need someone to perform a task, and imagine what qualities that person might possess. How, in a sea of people, can I find my ideal candidate?

In the past, I would have posted job ads on all the appropriate websites and braced for a flood of applications. I’d spend a weekend afternoon sifting through them all, deleting three quarters and writing follow-up emails to the rest. I always mailed a list of questions for each candidate to complete, with a deadline for their return. This enabled me to filter out at least another half who either didn’t reply in time, wrote dud answers or couldn’t spell and didn’t pay attention to details. Finally, I’d have 10 or so interviews. Often, they would all be disappointing.

My problem was that the best candidates all had good positions and were not reading job advertisements. Somehow, I had to find these people and convince them to take a risk by joining our start-up. The only solution seemed to be to hire a recruiter and, as a cash-strapped small business, we just couldn’t afford to shell out a recruitment fee of 20 percent of the candidate’s annual salary.

Earlier this year I signed up to LinkedIn’s Recruiter service. For $2,200 per quarter, I can run detailed searches on exactly the type of candidates I’m looking for and then approach them en masse. I can search by location, previous and current job titles, previous employers, which universities they attended and how long they’ve been in their current jobs. One of my biggest challenges since starting Posse has been the recruitment of high-quality developers: I’m not an engineer, so I don’t have a great network in this area. I know the people who apply through online job ads are seldom the best candidates, but we need to expand our development team.

Some companies, like Google, have a reputation for hiring the best developers. On LinkedIn I can run a search specifically for engineers who have worked or are currently working for Google in my area and have been in their positions for more than two years — so they might be looking for a new challenge. When I did this recently, I turned up around 90 results so I browsed through the profile headlines, eliminated anyone who seemed too senior to be interested, and then sent out emails to the 60 or so who were left. LinkedIn’s Recruiter enabled me to create personalized emails.

At least 60 percent of the people I contacted replied, and about 5 percent were interested in hearing more. I arranged to catch up with them for coffee and — if they were the right cultural fit — try to sell them on our vision for Posse and why they should join our team. I landed some exceptional candidates. In one afternoon, I was able to set up meetings with three senior developers who work at a large competitor of ours. I’ve learned that the more personal I can make the email, the more likely they are to reply. For example, I’ll search for candidates who went to a certain university and now work at a certain company. Then I can contact 50 candidates, but make the email sound like it’s been written just for them.

As a small-business owner, I recognize that building the right team is crucial. We only have room for A-plus players, who will always be in good positions and may require quite a bit of convincing to leave. LinkedIn gives us access to the passive job hunter market that used to be available only through expensive recruiters, and it helps us seek out top quality candidates from within other companies.

There is one catch. If I’m trying to poach the best people from our competitors, I can be sure that they’re trying to steal my best people, too. Once we turned down an acquisition offer from a competitor only to have the company approach all of our staff members individually on LinkedIn. This is almost impossible to prevent, but I’ve come up with a couple of strategies that may help. First, if your business is small, I see little benefit in setting up a LinkedIn page for it. Doing so just enables competitors to find and attack all your staff members at once.

Second, you can try to discourage your staffers from using the platform – although this is nearly impossible. When we relocated team members from Sydney to New York, a recruiter suggested that I ask our engineers not to change their location on LinkedIn because it would highlight them as fresh meat for the hungry New York recruiters.

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Obviously, it’s no fun to get fired. But it’s also no fun to be the one doing the firing.

I have heard it said that the stress of terminating someone’s employment can reduce your lifespan. I certainly know that I’ve awakened in a sweat the night before I have to have “the conversation” with someone. Or worse, I have put off the conversation and let the frustration and anticipation build for months. But no matter how bad it seems, it’s even worse for those being dismissed. The news you are about to deliver is likely to stick with your former employees forever; it will affect their sense of self worth and confidence in moving forward with their careers. Their colleagues and friends all know that someone assessed their value to the team and found it lacking. And after the humiliation at work, they have to go home and tell their families.

We’ve all heard the mantra “hire slow, fire fast.” As I’ve written in my previous posts, I’ve made lots of recruitment mistakes, but one thing I’ve always been good at is knowing when to let people go. I recognize that when someone doesn’t work out, it’s my fault for hiring them, and I try to make the process as pleasant as possible. I don’t want people running around saying what a nasty person I am, and I do feel responsible.

When entrepreneurs get together, we always seem to talk about how, if, and when to fire people. It amazes me how poorly most leaders handle the situation. They either procrastinate and hope people change (they never do), or they let them go in a way that leaves them feeling upset and confused. Getting this wrong can have disastrous consequences for your business. A friend has a media agency in California. He hired too many people too quickly and ended up with office politics and unproductive employees. He made a bold move by letting 40 percent of the team go at the same time. He called them into his office one by one, outlined why it wasn’t working and asked them to pack their things and leave immediately.

The employees gathered at a bar that afternoon to commiserate. They were angry and hurt. Alcohol-fueled tensions exploded, and they plotted revenge. Several contacted friends in the press and made sexual harassment allegations against the company. My friend’s reputation took a battering, clients jumped ship, and it took months before he could get the business back on track. He could have avoided this by hiring the right number of the right people, and if some didn’t work out, he could have let them go with more empathy. At my first company, I made all of the classic mistakes, including at least 20 hiring errors. That meant it gave me a lot of opportunities to practice what I have learned about letting people go with dignity.

I have gotten better. I’m not aware of anyone leaving Posse feeling disgruntled, and almost all of our former employees remain supportive of the company, come to our events and continue to advocate for the product. This is never an easy process, but here is some of what I’ve learned:

1. Let them save face

Whenever I sit down with people, I make it as obvious as I can what’s about to come. I ask them how they think their role is working out. I never make it about their personal contribution; it’s always about the role and how it fits into the organization. I lead them toward seeing that, in a small company like ours, their role isn’t quite what we need. I ask them what they enjoy working on and where they see themselves going in the future.

By this time, they know they’re about to be let go. I try to make sure they don’t feel as if it’s because they’ve failed, and I focus on getting them to think about what they would rather be doing. I think Posse is a great place to work, but we all have our own career dreams. You may think it’s dishonest not to be upfront and tell them exactly why they haven’t worked out. But by the time we reach this point, we will already have had several conversations about what’s not working and how they can improve. This conversation is about making a tough moment easier and helping ensure they have the confidence to move on with their life.

Once I had a senior employee who wasn’t right for Posse. I could see he was cracking with the workload and felt frustrated with the lack of clear role-definitions that he had been used to in more corporate roles. When I sat down with him, it was obvious he was exhausted. “Is this really what you want to be doing?” I asked. After a 10-minute conversation about his actual dream job (not here!), he decided to quit. He also asked if he could leave straight away and not work out his notice. This was a fantastic result. He felt happy and saved face with his colleagues, and I avoided the appearance of being a mean boss who just fired a member of the family, which always affects the remaining team. And we saved the four weeks notice I had expected to pay.

2. Don’t procrastinate

I remember the first few times I thought about letting someone go in my first business. I contemplated the decision for months, hoping things would improve. I put new reporting processes in place, tried new management techniques and wound up frustrated, procrastinating over what I knew deep down had to happen.

Other employees would be affected too. There’s nothing more demotivating for a team than to have people not pulling their weight and spreading negativity — and a boss who won’t do anything about it. In the lead-up to the big event, I would toss and turn in bed imagining how the conversation would go, how would I word it. When the day finally arrived, I’d be so burned out and angry that I’d fumble my words.

I’ve discovered that when I think someone won’t work out, they won’t. I can recognize when I’ve made a recruitment mistake within the first three months, and I’ll let them go within a week of the realization. I’ve found that the longer I leave it, the more they bond with the team and the worse the impact. It gives the person and the company the opportunity to move on.

3. Stick to any agreements. When in doubt, be generous

All of our employment agreements have probationary periods of three months. If the person is let go in that time, we pay one week’s notice. It’s important that there be no doubt about what the person should be paid. If there’s ever a question, I err on the generous side. It’s not good to look stingy, and I’ve learned that it’s important to do whatever I can to make the person leaving as happy as possible.

4. Be clear about what happens next and help them as much as you can

At the end of our conversation, I lay out the next steps. They’ll usually agree to go back to the office and hand over anything important to another team member, and we agree on how to explain the departure. They always finish up that day – it never works to have someone serve out their notice. We then talk about their plan to find another job. I ask if they’d like introductions to my contacts, and I offer to write them a glowing (but honest) reference. I wouldn’t write anything that’s untrue, but it’s always possible to find positive attributes to fill out the letter and help the person find a more appropriate job.

5. Announce it to the team together and let them say goodbye

We go back to the office and call the team together for the announcement. We almost always paint it as the employee’s decision. I just stand there while the person explains. I thank them for their contributions, and we all go out for a drink. The drinks are usually a bit awkward, but it’s important to let the remaining team members grieve. They’ll all go out and drink together anyway, and I’d rather be there than not. Letting someone go is one of the toughest and most important things entrepreneurs have to do. We know that the business will succeed or fail on the strength of the team, and a team is only as strong as its weakest member.

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I met recently with a large Silicon Valley venture fund. My company is not raising money at the moment, but the fund had heard about Posse and reached out to me online. Since I was in town anyway, I decided to meet with the fund’s investors and build a relationship. I showed them some slides and talked about our vision for Posse. They seemed engaged. They asked questions about the various insights we’d gained and pivots we’d taken. And then one of the executives leaned toward me and said, “You’ve shown a lot of persistence. Just like when you were seven years old selling flowers on the side of the road.”

His partner then started talking about my experience building a radio station in my early 20s and the various bands I’d managed in Australia. I was floored when they asked me whether, before our meeting, I had done the power pose I had written about in a previous blog post about body language. Two senior executives from the other side of the world knew my life’s story and didn’t mind reciting it. I felt naked.

The first time anything like this had happened to me was four years earlier, when I met with a music company in New York. That time, someone whom I didn’t know asked about an event I’d organized several years earlier in college. The question was relevant but a surprise — he had researched me on the web before our meeting.

That night, I did a web search for myself for the first but not the last time. I discovered links to a handful of articles that mentioned episodes from my time as a band manager. Some related to nonprofit work that I’d done but all too many quoted me saying “no comment” following misbehavior by some of my bands. That was not the brand that I wanted to present. Knowing that such web searches before meetings would become more common, I decided to take control of my online brand. Here’s what I’ve done.

1. Think about why

If your only concern is that people will conduct searches on you before meetings, you may just need to create a LinkedIn profile so they will find something that you want them to see. For me, though, the purpose of building an online brand was bigger. I wanted to raise the profile of my company in order to win clients, attract users and raise capital.

I have also decided to be open about the company’s struggles so that those who are interested will come on the journey with me. As a result, they are more likely to be supportive, rather than critical, when we experience those inevitable difficult times. Finally, I wanted to raise my personal profile to set myself up for whatever I decide to do next.

2. Define your brand

In 2008, a close friend shared with me a notebook in which he’d written down his personal values. This made me think a lot about my own values, and I decided to write mine down, too. The process forced me to focus on who I was, how that would affect my decision-making and what persona I would project to the world.

As entrepreneurs we create brand values for our companies but often not for ourselves. By writing down my values, I defined my personal brand and made it easier to make sure that my values are projected across everything I do online. This included the way my own blog is written, the types of other publications I write for and what I post in social media. As with a company brand, I try to ensure that the message is consistent.

3. Understand that social networks are the new calling cards

If you are on social media, people are going to check out your profiles. LinkedIn, Facebook, Twitter and Instagram will come up first, often in that order. LinkedIn is a great opportunity to showcase your achievements and connect with prospective partners and clients. I now do all of our recruiting through LinkedIn, searching  through profiles based on current or previous employment. When I reach out, I’m aware that everyone who considers replying will read my profile, too. On Facebook you can set your posts to private but, since my brand is about being transparent, I’ve made my profile public. Of course I have to be careful not to put stupid photos up.

An old boyfriend once became annoyed with me because I refused to set my Facebook profile to “in a relationship” with him because I was embarrassed by some of the photos he had on his profile. The photos weren’t of me, but I worried about how they would reflect on me. Maybe I was too sensitive (he certainly thought so).

4. Pay attention to what comes up first in Google

One reason to write a blog with your name in the URL is that it’s likely to pop up first on any Google search. It’s also helpful to have a name that isn’t common. I’m lucky with my first name, which has a less common spelling, and my blog ranks high if you search “Rebekah Campbell.”

If I had a more common name, I might elect to include my middle initial to make it easier for people to find me online. I would try to get the .com URL address for the name and then build sub pages using other terms that people might search for when looking for me. For example, people might search for “Rebekah Campbell Posse” and so I have a web page at rebekahcampbell.com that should rank first if anyone searches that combination of words.

If there were bad things written about me online (there aren’t), I would try to create new listings that would rank highly in Google and push the old links to the second page of search results. If you search your own name and nothing comes up, or if an early link displays something you’d prefer to keep under wraps, consider creating a LinkedIn page. It always surprises me when I see politicians who have problem headings on page one of their Google results don’t have a LinkedIn profile.

Of course, transparency does have its downside. In the same venture capital meeting I mentioned earlier, one of the executives brought up my interest in American politics. He suggested we might want to discuss my views at a future meeting. I smiled and, without thinking, let it slip that I’m looking forward to 2016 and that I’d love to work on Hillary Clinton’s campaign. The room went silent, and I could tell instantly that they didn’t share my enthusiasm.

Over all, I’ve found building an online brand to be a great investment in time. It can be disconcerting to be reminded that anyone who’s interested can find out pretty much anything they want about me online. But the positives have outweighed the loss of privacy. In any case, I don’t think any of us can choose not to pay attention to our online brand.

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