The founder’s journey: ten questions for reflective thinking

The founder journey is tumultuous, filled with wrong turns, elation, failures, enthusiasm, doubt, hardship, success, conviction, hope and luck. Wow that’s a list! It reflects the emotional roller coaster you face as a founder, highs on some days and lows on others, sometimes both in the same day. 

Every founder yearns for success and despite the challenges, they don’t let go of their dream easily. Founders are convinced that only they can lead their start-up to success. I’m the one with the vision and the desire to build a great company. I have to be the one running it several entrepreneurs have told me. Whilst there is an underlying truth to that view, it’s not necessarily the case for all ventures.

At the start, the enterprise is an embryonic idea, an intuitive hunch in the mind of the entrepreneur, who having done some research, gathers insights and sees the potential of the opportunity, the innovative product, service, or business model to capitalise, and about who the potential customers are. The founder builds the venture with that vision, taking great pride in their founder-CEO status.

New ventures are personal labours of love, and founders often become emotionally attached, referring to the business as ‘my baby’ and the team as ‘my family’, using parenting language without even noticing. But whilst this emotional attachment acts as rocket fuel, unless they have relevant skills, judgement and experience, there comes a time when they become blinkered by their passion and belief.

Founders’ attachment may be necessary to get new ventures up and running, but overconfidence, and naivety can later create problems. Great founders eventually realise that their acumen isn’t enough for their venture to capitalise fully on the opportunities before them. Paradoxically, the need for a change becomes even greater when a founder has delivered results. Let me explain why.

The first major task in any new venture is the development of its product or service. Many founders believe that if they’ve successfully led the development of the new offering, that’s ample proof of their management prowess. Since I’ve got us to the stage where the product is ready, I can lead this company to the next stage is a common refrain.

Their success makes it harder for founders to realise that when they celebrate the shipping of the first products, they’re marking the end of an era. At that point, founders face a different set of challenges: to build a company capable of selling large volumes of the product and scaling the operation. Finances, people, and marketing – aspects of the business model a founder can lead and shape at the outset – become more complex.

The organisation has to become more structured, a scalable business model of processes, and develop specialised roles. The dramatic broadening of the skills that the founder needs at this stage stretches most founders’ abilities beyond their limits. Also, they may have bootstrapped to date, but now they need external funding to provide growth capital.

The faster founder-CEOs lead their ventures to the point where they need outside funds and new management skills, the quicker they need to reflect upon their suitability to lead the business. Success makes founders less qualified to lead the venture through the next growth phase, and they are vulnerable. The founder’s moment of truth sometimes comes quickly.

Founders who are motivated more by creating value will recognise it’s time for change, by contrast, founders motivated by control are more prone to making decisions that enable them to lead the business at the expense of increasing its value. Choosing between value and power allows founders to identify what success means to them. Once they realise which way they are turning, founders must, as the old Chinese proverb says, decide on three things: the rules of the game, the stakes, and the quitting time.

This is where reflective thinking is important, analysing what you’re doing, what you’ve done, what you’ve experienced, what you’ve learned, and how you’ve learned it – and what you want to do – then taking all of this and making a judgement call on what is needed in the next step of your journey.

Reflection starts with self-awareness, being in touch with yourself and what’s shaped your worldview. From this, the next step is self-improvement. Once you’re aware of where your strengths and weaknesses are, you can know where to shift your focus. Then there is the brave decision of empowering yourself to take control and make the necessary changes in your startup life – do I go again, or is it time to step away from day-to-day leadership of the business?

Reflective thinking means taking the bigger picture and understanding consequences. In doesn’t just mean jotting down what you did or plan to do in the future. It means considering why what you did or plan to do matters, to help you better understand where you are today, exploring emotions, feelings, reactions, and knowledge. It should be cathartic, exploring the ‘so what?’ instead of just the ‘what’?.

It means truly trying to understand why you did what you did, and why that’s important. This often includes delving into your feelings, reactions, and emotions, and then looking ahead considering the larger context, the meaning, and the implications. In essence this is the Know Thyself maxim, attributed to Socrates.

The principal meaning of the phrase in its original application was ‘know your limits’, either in the sense of knowing the extent of one’s abilities, knowing one’s place in the social scale, or knowing oneself to be mortal. For founders, it’s useful as a simple phrase to nudge us to appreciate the true value of self-awareness.

Research suggests that when we see ourselves clearly, we make sounder decisions, build stronger relationships, and communicate more effectively. Self-awareness is probably the most underrated key to a much better startup life.  Self-knowledge, self-realisation, and self-scrutiny are key traits of successful founders, albeit actioned in an often messy and unpredictable way. It’s also illusory for us to think it ever stops, I would urge that understanding yourself is a lifelong task.

It’s really important, as a big barrier to founders achieving anything is hubris, thinking that we do know, often confusing our confidence in our opinions with thinking that confidence is an indication of my degree of correctness. We feel sure and take that surety itself to be evidence of the truth of what we think. That’s a cognitive error, fallacious reasoning. We should ask ourselves and acknowledge the infirmity of our beliefs and the paucity of our knowledge; the fact that opinions we have might just be opinions.

As a founder there is always a move to make and a hand to play, decisions to face, but to Know Thyself requires a more intrinsic approach, so I have developed ten questions to provide a framework for reflective thinking.

1. Am I being consistent? A startup is an adventure, seeking a solution to a problem, but what I see in too few founders is an ability to retain focus and stick to the one thing. Everyone on the team needs to know what the goal is and what the expectations are. Founders that zigzag just create confusion. As a founder, you need to make sure you are consistent in your direction of travel.

Takeaway: the moment you let up is the moment you progress. Can you stop changing your mind?

2. Am I being too optimistic? Founders need to have the glass half-full mentality, but being overly optimistic is dangerous. We romanticise about venture building, but in practice it creates detachment from underlying reality. Undue optimism quickly translates to plans lacking a realistic chance of success.

Takeaway: can you avoid hallucination to enable execution?

3. Am I being too pessimistic? Conversely, there’s a fine line between being realistic and being negative. To be realistic (and not negative) means maintaining a vision of the opportunity in the face of turbulence and being disciplined in the pathway to achieve the opportunity.

Takeaway: this approach builds credibility; do you have the right balance?

4. Am I being passive? Founders have to get into the long grass and detail every now and then, rolling their sleeves up and sorting stuff out. Every issue starts as a distant, far away rumble, but builds to a loud roar on your doorstep if not addressed. I’ve learned (the hard way) that being an active founder is ultimately always better for the venture and the team, no matter how uncomfortable it is in the moment.

Takeaway: Are you ‘hands on, hands in’ when needed?

5. Am I being arrogant? If you think you’re right and someone else is wrong, ask if it’s because you have better information, judgement, or instinct. Founders don’t by rights have all the right questions, let alone the right answers. In my experience, being more openminded to the input of others avoids missing something that could lead to a better outcome.

Takeaway: Are you capable of building a team and letting their voices be heard?

6. Am I letting perfectionism get in the way? Focus and attention to detail are vital, but through experience working with founders I’ve seen that they can’t help themselves, adding one more feature to the MVP, or one more sentence to the crafted marketing blog. This can be paralysing to the team. Seek, the optimal balance, which means getting the little things wrong and the big things right.

Takeaway: can you get comfortable with being uncomfortable?

7. Am I overthinking this? Every substantive decision has pros and cons. Analysis is important, but over analysis leads to paralysis. Having a bias towards action and moving in the right direction versus endlessly analysing is what a founder needs to focus on , especially when most decisions are reversible.

Takeaway: can you trust your instincts and go with them, first time?

8. Am I focusing on the input or the output? As with every aspect of reflection, there are two perspectives to consider. Here, there is a combination to consider:

  • Bad input, bad output = Incompetence
  • Bad input, good output = Luck
  • Good input, good output = Repeat
  • Good input, bad output = Keep going

Takeaway: Can you stand back and unpick what’s working and what’s not?

9. Am I taking enough risk? This can be overwhelming. Risk pulls you in and out of your comfort zone, but growing a startup isn’t linear with the revenue chart always ticking up to the right – it takes big steps and good timing to cross the chasm. Too little risk means short term comfort but long term pain in terms of what could have been.

Takeaway: Do you have the mindset for making bigger and bigger bets?

10. Am I leading from the front? If you want  your team to be all in every day, you have to set the culture. Nothing builds respect like showing up. This isn’t the easy part of entrepreneurship, but it’s by far the most impactful. 

Takeaway: Are you comfortable in a hair shirt?

Not every question applies to every circumstance, but many of them overlap, and I believe offer a balance between a founder seeking self-awareness whilst assessing the future needs of the business. Knowing yourself is not only the most difficult thing, but often the most inconvenient one too.

One of the founder challenges in startup life is to be your own person and accept who you are, and not try to be someone you are not. A founder who knows who they are eliminates noise. To be effective, a founder must be selective and honest with their time and energy, because both elements of startup life are limited.

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