The communication that can save money for your investors and produce a better outcome for your company

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If you raise a problem, will your cofounder bite your head off?

You probably saw it reported a few months ago: another sale of a successful SaaS startup. The price was undisclosed, of course. But there was lots of happy talk about how excited the founders are to be joining forces with the buyer, and how great the combined business is going to be for their customers.

What you won’t know, unless you are one of the startup’s investors, is that this declared triumph hides a failure — one that’s all too common, and has lessons for founders of many other startups. Because the selling price wasn’t what you imagined: actually, the company went for barely one-quarter of all the cash that had been poured into it. So while the VCs in the most recent funding round got most of their money back, all the earlier investors got a big fat zero. And the founders who flogged their guts out to make it a success (let’s call them Gordon and Ajit)? Their shares were worth nothing. …

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The value of communicating objectives clearly

A checklist of five things that can help you make sure your team are rowing in the same direction and in the same rhythm

In one of my favourite cartoons, Dilbert’s pet dog asks him: “How was work?”

“Are you being sarcastic?” Dilbert demands. “You know my life is an endless series of useless tasks orchestrated by idiots. Why do you even ask?”

“I like hearing it,” says the dog.

“Your honesty is not refreshing,” replies Dilbert.

Not many of the CEOs I coach have this problem. Running a venture-backed startup is a job that gives you a strong sense of purpose, a feeling that you’re learning new stuff every day, and great autonomy in how you do things. So when you’re at the top of the pyramid, it takes some effort to understand how things feel further down. From the founder’s desk, the company’s strategy often seems clear as glass — and the connection between the mission and everyone’s jobs is unmistakable. Some tasks may be boring or repetitive, but they’re usually either part of the business model (eg driving for Uber), or a temporary measure that’s part of a ‘concierge MVP’ — where the company is doing something by hand now which it expects to automate in future, because you learn a lot from having people do something manually before you write code to do it. …

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If only life were a bit more ordered…

What startup CEOs can learn from a neurosurgeon and an Asian noodle restaurant about how to manage their work better

There was a time when I was a CEO — I think it was while our company was growing from 25 to 50 people in the space of seven months — when I began to feel overwhelmed. It wasn’t just the ever-broadening range of things I was expected to do in running a growing business. It wasn’t just the queue of people that formed by my desk wanting to discuss stuff or check something. It wasn’t just the to-do lists that kept getting longer. …

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The green shoots of managerial communication

Applying methods from suicide prevention in fast-growing startups, and five questions to help solve business problems

The email came in from Jonas, one of the smartest CEOs I know. “I’m having real trouble with some of my one-on-ones,” he said. “It happens with people who are shy and not particularly open. But I have to keep asking them questions, and they mostly give answers that are really short and to the point. How can I get them to have a proper discussion?”

Jonas isn’t alone. A number of the startup CEOs I work with have found it hard to get their team to talk to them. A few people will ask for guidance and input on every single tiny thing. Others get very defensive very quickly — or like Jonas’s people, they close off discussion by giving out the least possible information. And some, when asked direct questions, will respond with generalities like “Don’t worry, it’s all under control.” …

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Is your trusty steed default dead or default alive?

Five questions to help decide whether a slow-growing startup should raise more money or give up

Twelve years ago, I went to fundraise for a new startup from a guy who’s a successful and effective operator in the European technology business. The meeting was a perfect illustration of the saying that ‘if you want advice, ask for money; if you want money, ask for advice’. I asked him to invest, and he explained in brutal detail why he wouldn’t invest and didn’t think the business would succeed.

That was the advice; I didn’t take it. His reaction was based on half an hour’s thought. I’d done probably one hundred hours of research on the issues we were discussing, and I thought I knew better than he did. So I went ahead and raised a bit over a million, and started the business. And every time I met him over the next 18 months, he’d ask me the same question: “Are you still flogging that dead horse? …

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Are you the boy or the donkey?

Five ways to get the people who report to you to work harder — three of them good, and two of them bad

One of the fascinating things about coaching CEOs is that there are things they feel able to talk about that are almost impossible for them to discuss with their investors and board members. Partly this is because board members have a fiduciary responsibility to shareholders, which has to include deciding whether the company’s current CEO is the right person to lead the business in future. So confessing failure, mistakes or incompetence to a board member can be a severely career-limiting move. …

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Guilty of sin number one!

It’s not only when a startup is going badly that founders can get things wrong. Here’s a list of the biggest risks CEOs face when business is booming

There are three things I feel guilty about in my business career. The one I’m ready to admit to today is this: I made an unnecessary trip on Concorde.

It was 1999, the last year of the first Internet bubble. The company I’d founded was on track for an initial public offering (IPO) within a few months, and I had a scheduling conflict: we had a board meeting in London set for one afternoon, but I was speaking at a conference in New York the next morning. It was too late for the last flight to New York, so it looked like I had to choose: move, miss or dial into the board meeting, or cancel the conference presentation. But there was a third option: go to the board, get a good night’s sleep at home, and take the Concorde flight, which left Heathrow the next morning at 10am and arrived at JFK, magically, at 8.30am

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An executive’s idea of a wise investment in your startup’s growth?

A simple two-by-two approach to decide what kind of people to recruit for a growing startup, and to avoid the most expensive hiring mistakes

When founding my first serious startup, I made enough mistakes to fill the Encyclopaedia Britannica. But the most useful early mistake, as a learning opportunity, was that three of my first four hires were gone within ninety days. One of those was the head of marketing — let’s call her Michaela.

Michaela had a stellar CV. She’d been to a top university. She had a decade of career experience in the industry. And she’d worked for two of the top agencies in the world. She was way out of our league, and so expensive that the only way we could bring her was to pay half her current salary and to give her a huge slug of stock options to outweigh the loss of the other half. …

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COPPER: helps you to concentrate on one big thing

If you’ve found that the pressures of juggling lots of projects and managing a team have made it harder for you to do deep work, here’s how to find the way back

“Tim, I badly need your help,” said Lionel. “I’ve been observing for the past week, and things are much worse than I realised. It’s actually down to ten minutes.”

The story that emerged from our coaching session was this. Lionel runs a highly successful venture fund (I work with VCs, as well as CEOs). He has a strong team, and a load of investments in hot startups. He’s also got lots on his plate. New deals to look for. Portfolio companies to help. Exits to organise via IPOs and trade sales. …

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The collateral damage from a troubled startup

Heavy work pressures can infect any long-term relationship. Here’s how to stop the rot — whether you’re a CEO or not, and whether you work in a startup or not

It took a question from my three-year-old son one morning at breakfast to make me realise how much harm my startup was doing to my marriage. The night before, I’d come home late from work (as usual), tired (as usual), stressed (as usual), and in a filthy mood. And I hadn’t been very nice to my partner.

For the past two years, as I’d been building a startup and taking it towards an IPO, she’d been a model of calm, patience and kindness. But when my behaviour finally crossed a line, she wasn’t left with many options. I was in the kitchen, being mean and nasty about something, and stepped outside into a closed-in patio to smoke a cigarette (yes, the need to do that was a symptom too). So she… locked me out. Then she opened a window on to the patio, looked me in the eye, and said, “You can come back in when you’re ready to be reasonable.” …


Tim Jackson

Startup founder, former Economist and FT journalist, CEO coach, and seed VC at

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