Stop telling entrepreneurs what to do. Start helping them think

Everyone has an opinion, advice is everywhere. It’s what to do with it that’s hard. If we really want to help entrepreneurs grow into the best CEOs, then we should stop telling them what to do and start helping them think. Because, in a VUCA world, it won’t necessarily be the entrepreneurs who have more information who will be leading the most successful businesses of the future, it will be those who develop their ability to think and act in more complex ways.

Let’s explore what it takes to transition from being a founder to a CEO, including the problem with “how to” advice and the benefits of becoming an independent thinker in a complex world.

Don't tell entrepreneurs what to do, help them think

From founder to CEO

Stefan Manku is the founder of TalktoStefan, a listening service for founders (full disclosure, he’s also a client of mine). He identifies two types of business challenges:

1. Technical problems occur when there’s a gap in your knowledge. To solve these you need information. This is where friends, investors, peers, business books, courses and mentors will be able to help. You don’t know what you don’t know and you need someone who does to tell you what to do.

2. Mental blocks occur when too much information is the problem. You have too many options and don’t know which way to go. Your brain is stuck in endless rumination and you just don’t know what to do*. You already have the answer, somewhere in your head, you just can’t pull it out from the swirling mass of your thoughts. For these problems the solution is not more information, like it is for technical ones, it’s sifting through what you already have and discerning the signal from the noise.

When it comes to leadership, there’s a third challenge:

3. Transformational growth is what is required if you want to shift from being an entrepreneur into a true CEO. It’s difficult to achieve this from a Tweet or blog post from you favourite investor. It requires you to confront more existential questions like “what sort of leader am I now, and what sort of leader do I want to be in the future?”  It requires you to explore and solve problems in more systemic, interdependent ways. Transformational growth occurs not when you increase what you know, but when you improve how you think.

Thinking for yourself means finding yourself, finding your own reality. Here’s the other problem with Facebook and Twitter… When you expose yourself to those things, especially in the constant way that people do now—older people as well as younger people—you are continuously bombarding yourself with a stream of other people’s thoughts. You are marinating yourself in the conventional wisdom. In other people’s reality: for others, not for yourself. You are creating a cacophony in which it is impossible to hear your own voice, whether it’s yourself you’re thinking about or anything else. That’s what Emerson meant when he said that “he who should inspire and lead his race must be defended from travelling with the souls of other men, from living, breathing, reading, and writing in the daily, time-worn yoke of their opinions.” Notice that he uses the word lead. Leadership means finding a new direction, not simply putting yourself at the front of the herd that’s heading toward the cliff.

Solitude & Leadership, by William Deresiewicz

Content overload and the ‘how to’ trap

It’s not that we don’t all need good, timely advice. When you set out to build a business from scratch there’s just too much to know and learn. So it makes sense that, for all but the most experienced serial entrepreneur, this advice would be helpful. It’s just really important to be aware of the pros and cons of that advice.

Almost all the literature, and there is plenty of it, targeted at startup founders and entrepreneurs provides prescriptive solutions based on previous experiences. Most start with “How To” The rest follow a similarly predictable pattern:

Do these 3 things…
Avoid doing these 3 things…
Adopt these rules to…
This secret formula will guarantee…
These 5 steps will guarantee…
Follow this [Playbook / Blueprint / Formula] in order to…

The inference is simple: ‘follow this advice and you’ll be just fine’. But for the complex task of business building and personal development, there are no hard and fast rules, no secret formulas, and certainly no guarantees.

Any advice comes with nuance that’s rarely discussed by the authors. Advice is always highly context dependent and just because a particular strategy, tactic, or other course of action led to success in the past, doesn’t mean that it was the only reason for previous success, that it will work again in the future, or that it accounts for luck, randomness or other features of the complex world we live in.

Here’s what three experienced entrepreneurs, executives and investors have to say:

This is what’s wrong with most of the business literature as they try to put it into some framework like here are the three steps you need to go Good to Great, be a Built to Last , or whatever Jim Collins says. Because it’s not like… it’s very situational. It’s very specific to your company and your product and your market and your people and all these kinds of things.

And so, yes, the things that you are doing, you have to understand it at a different level [emphasis added]. There’s not the ABCs of building a company. You can follow the 30 steps of building a company that anybody puts out and get nowhere all the time.

Ben Horowitz, on the Masters in Business podcast

In my fourteen years on the executive team at Netflix, we constantly faced such daunting growth challenges, sometimes existential ones, and in technologies and services that were pioneering. That was no playbook; we had to make it up.

Patty McCord, former Chief Talent Officer at Netflix, in Powerful: Building a Culture of Freedom and Responsibility (Amazon UK, US)

You can ask for tips, but you can’t adopt someone else’s approach in aggregate. More than anything else, the journey of building a company is really the construction of your own one-of-a-kind playbook to build a team, culture, and product.

Scott Belsky, in the introduction to A Dozen Lessons for Entrepreneurs (Amazon UK, US)

Think like a CEO

Much advice caters for solving technical problems. That’s helpful and necessary, but even then (broken record alert), it’s important to remember that all advice is context dependent and, just because something worked in the past, doesn’t mean it will work in the future. Here’s some questions to ask yourself next time you read a “How To” article:

  • Who is giving it? Are they reputable?
  • What’s the context against which this advice was written? Is it relevant to me and my business right now?
  • What about this article do I agree with? What don’t I agree with?
  • Which bits are helpful and might I want to use? Which bits aren’t relevant and do I want to ignore or discard?
  • How might this article be wrong?
  • If I follow this advice, what might the second, and third, and fourth order effects be?
  • Thinking about the answers to all these questions, what do I really think and what am I going to do?

No entrepreneurs begin their journey as a world class CEO. Thrown in at the deep end, with almost no previous experience or training, they must learn on the job. Advice can help them solve technical problems, but the best entrepreneurs, supported by extraordinary mentors (and sometimes coaches), develop the capacity to think and make sense of their situation in new ways, pushing through their own mental blocks and growing in transformational ways.

A lot of people think about entrepreneurship content in terms of hard skills and tactics. How do I drive viral growth? What is the secret to better SEO? These hard skills are important, but entrepreneurs can benefit from softer learnings as well.

Entrepreneurship and Loneliness, by Reid Hoffman

The shift from founder to CEO requires learning hard skills and tactics, and ‘softer learnings’ like self-awareness, self-regulation, motivation, empathy and social skills (the five pillars of emotional intelligence). But it also requires vertical development: transformation in the leader’s underlying capacity to make sense of and respond to situations, working directly on their internal ‘meaning making’, rather than just behaviours or actions.

That’s because, as we develop in our adult lives, we come to view ourselves and the world around us in new ways. We see the bigger picture, appreciate change and interconnectedness, navigate complexity, see things from new perspectives, and better understand ourselves and our own reactions. Evidence suggest that that’s where we see our true growth edge and truly develop as leaders. None of us will get there though if we’re constantly fed information and we don’t learn to think for ourselves.

* The word “ruminant” comes from the Latin ruminare, which means “to chew over again”. Animals like cows, goats and sheep process food cyclically through their uniquely designed digestive system because they struggle to extract sufficient protein from their plant-based diet. Whilst it is a fantastic evolutionary strategy it doesn’t serve human beings well.


More articles to help you think more clearly:

Want to be a better tech leader? It’s complex. is the follow up to this post, exploring the different type of leadership required in complex, not complicated, world.

What’s the difference between a coach, mentor & therapist explains why, like any high-performing individual, new leaders need to wrap a professional support team around them to give themselves the best chance of success.

What is the difference between coaching & mentoring? explores the subtle but important difference between these two approaches.