How to become a radically self-honest founder

The value of radical self-honesty

Seeking to hit the moonshot to revolutionise the world is never easy. It’s hard to know in advance whether you’re just deluding yourself, or whether you’re really on track to make the impossible possible. 

Credibility has become your foundational currency, both with yourself and with others—including your co-workers, your investors, your customers, and anyone else you want to bring on your founding journey. 

You are going all-in, staking your time, effort, and yes, even your reputation for this business venture—the last thing you need is for self-deception to seep in and ruin it all. The reality, however, is that humans are prone to lie to themselves, especially during complex, high-stakes, uncomfortable situations.

The good news is that by recognising that potential in you, you are now in a better position to prioritise self-honesty above all else. Make a commitment and conscientious effort to be radically transparent and forthright, above all with yourself. 

By being radically self-honest, you earn trust in your own judgement and convictions, and are better able to make others trust you and help you build your startup. 

As you embark on your journey towards radical self-honesty, Gena Gorlin shares 3 key steps to make this stick: 

Step 1: Write it down 

Start journaling daily to hold yourself accountable.  Ask yourself the really hard questions to identify your insecurities and potential pitfalls, and have it written down pen to paper and reflect. 

You can think of this as a reflective “self-coaching” exercise of sorts, where your objective is always to first listen to your “inner players” to better understand what they think, feel and need in a non-judgmental way before going to “what’s true” and “what’s next.”

How this works practically could be as simple as starting with a factual recount of that burdensome situation. Then identify your distinctive emotions that show up. Observe what your called-up emotions are saying, how they are saying it, and what they are telling you to do. This is also where you can check for any lies they might be telling you (like telling you you’re angry when you might actually be feeling scared or hurt). Dive also into your underlying core beliefs – why are you thinking and feeling this way? What assumptions are underneath that? And underneath that?

Next, leverage your analytical mind: look into all the knowledge and facts you have about the situation. This will help you form an honest, considered judgement about what you do and don’t know and what you ultimately want to do.

Jot all of these down, line by line. 

So, for instance, it could be that you might feel very guilty, having to break up with a co-founder because the team is not making progress – that’s your first line. Then consider the facts around it and write them down. This could be like “EF has an 8-week time period for us to experiment with co-founder matching,” and you might get clarity and confidence to go ahead to have that difficult conversation. Or you might discover that you actually have good reasons for not wanting to break up with this co-founder yet, but that you want to try pivoting to a more exciting idea together.

Or maybe it’s actually the fear of having no alternative to pair up with. Write down, “I am fearful of breaking up because I don’t want to leave without a co-founder.” Look next into the facts and you recall that you also spoke to four others that are just as impressive. Write their names down, why you think they might be a good fit, and your game plan to ask them to co-found with you. And you will have the belief to break up and take another stab at finding a better business partner. 

In general, by calling your emotions out, you become more cognizant of them and how they are affecting you, and this gives control back to you; you are no longer at the beck and call of your emotions, but rather can use them as inputs to your own conscious reasoning process.

Step 2: Find a trusted person who knows you

Sometimes, the people who aren’t involved will see the bigger picture best.

It could be a trusted friend, mentor, or former colleague; basically, someone who knows you for you and isn’t in the thick of what you are doing. 

Let them know you are starting on this exciting but ambitious venture and you want to be a founder who is radically candid. Schedule regular meetings with them and be very open with your comments, questions, and viewpoints as you share your daily ongoings with them.

They can play the role of the devil’s advocate, questioning your motives and asking the hard questions. These could include questions like: 

1. Are you actually happy working with your co-founder or are you just afraid of facing reality?
2. Could you be overselling and why? 
3. Could you be underselling and why?

These questions can reveal deep-seated beliefs you have due to your past experiences that only you and your friend know about. Maybe you are misjudging your co-founder because of your previous failure; By having honest and reflective conversations with a trusted confidante, you’ll be back on track and continue to make better and more informed decisions. 

We all have our own blind spots. By having someone we trust to further augment our journaling process, we uncover them, leaving no stone unturned for better decision making. 

Step 3: Check in with your co-founder too

Founders have plenty to do; daily check-ins only solve short-term challenges. Dedicating a separate fixed regular time to have those uncomfortable conversations will help to build up your working relationship. It keeps both of you accountable to be radically honest with each other and is definitely more healthy in the long run. 

For instance, any delay in giving constructive feedback on customer research can easily slow the speed your team is moving. Any delay in having that conversation to better understand each other’s motivations and working styles can result in bigger misunderstandings. The list can go on but what’s clear is the earlier you have those conversations, the quicker you sort those out and you become a better team.

“It’s one of the costliest founder mistakes that keep cropping up,” shares Gorlin.

“I’ve seen founders at various points in their entrepreneurial journey putting off hard conversations for the wrong reasons.

And instituting regularly scheduled “honest conversation” times is one of the easiest ways to go about it. It forces you to make time to give critical feedback, sort out disagreements and deliver the bad news.”

So what should founders chat about during these conversations?

It’s a time for founders to ask, “What should I know that you are not telling me,” and be given real, authentic feedback. Maybe it’s about the way one founder is doing customer research, and it is during these check-ins, they can go deeper into how customer research is done, and why it is done in a particular manner. Sometimes it might also be a really nice, sincere compliment that you or your co-founder wouldn’t have otherwise thought to verbalise. 

It’s a time to unlock preconceived notions founders might have about each other and help each other be accountable to be radically honest, in order to chart the best path forward as a team. 

What’s critical is to remember that Rome wasn’t built overnight, and it’s the same with cultivating self-honesty. Human tendencies to self-deceive don’t stop, and founders have to build the daily discipline to journal, reflect, schedule honest conversation times to grow in self-honesty. It’s the accumulation of little things that drive the eventual massive impact.

If you’re interested in learning about the psychology of founding a company, listen to our new podcast series, ‘The Founder’s Mindset’.