“I think he is after my job as a CEO”.

“How-do-you-feel dinners”

“I think he is after my job as a CEO”. His voice almost trembled, and it was those words that made it apparent that this startup was no more. “I mean — he challenges everything I say and just because we haven’t signed the agreement with Huge Customer A, he doubts my skills! You know how highly I hold him — he is the best CTO one can have, but…”. I sighed and finally interrupted “I think you are just completely out of sync — I think you missed an essential thing the last year, and now it might be too late.” I didn’t wait for his response and continued “you have to sit down with a bottle of wine.”

Needless to say if a founding team gets out of sync or start to holding grudges towards each other the “innovative process” is far from optimal. At my first company TAT (www.tat.se) we were six founders — with rather different backgrounds and values and we created the concept “wine evening”. Every quarter (at least) we had a very casual dinner at one of the founders’ place and shared one or two bottles of wine. The agenda was very simple — with just three bullets:

1. How do you feel about your personal life?
2. How do you feel about work?
3. What should we do different according to you?

One person started — with the first point only — and handled that to a great extent. Everyone else listened and the only thing the others were allowed to say were questions to get the speaker to handle the subject. (If you know your founding team you know that some people might reply either “fine” or shrug at the first question in particular.) And if a discussion appeared then we let it continue for a short while and then all tried getting the attention back by re-asking the person who should be talking “John, how do you feel about your personal life?”

Once the first person had handled the first question the second person took over. If we really felt like it we took notes, but made sure that no-one was appointed “secretary” or “chairman” but that all were equal. (Nowadays there are so many good recording apps so I guess recording it would make the most sense.)

By making sure everyone was aligned with the personal things we could much easier move into second base — work. Because usually during the first bullet work trickled in — someone was envious of that another person got to meet VCs / focus on R&D / travel a lot / avoid traveling / etc. And that envy was not “work”, but usually things like being able to focus, getting the most interesting experience, not having to be away from family, etc. When these things came to the surface then it was easy to resolve — much easier than a discussion about titles or responsibilities as often these are proxies for personal things.

I truly believe that by just talking about how you feel in the first question then this discussion became a lot more fruitful. It is hard to argue with a person “feeling left out”, “fearing that we would run out of money”, or “feeling overworked and being the only one responsible for the quality of the code”, but very easy to argue with the plan of hiring another developer — which might solve any of the three issues.

The second question usually blended into strategy — if we spent too much right now, or were too bold (or too restrictive) in our goals, etc. As a lot of the personal matters were handled then this often became a lot more tense — but this is where you have gotten one glass of red wine already so the discussion is a bit more relaxed.

The last part was where we actually took notes. Here it usually became a discussion. This discussion is where most other discussion like this starts. But then ego is not left by the door — as people don’t really have a common ground. By starting with the lowest levels — how each person feels — you avoid all “jump to conclusion” results and by not scheduling a two-hour meeting to discuss company strategy on a Friday afternoon, you can avoid starting a weekend with shouting. And by syncing personal goals it becomes a lot easier not to get out of sync on the bigger things.

This is something I recommend all founders. Now with my current company (www.brisk.io) the founders have small children so sometimes not only can it be hard to find the evenings, but people may be too tired then, so we do “How do you feel lunches” every second month — you have to compensate for the loss of wine ☺

So, what happened to the co-founder & CEO who feared that his co-founding CTO didn’t agree with him? They sat down, all three founders (and me, actually, to get them to do it), and after just an hour it was even more apparent that they couldn’t have been more out of sync. About what the product was about, about what should happen the coming months, but most of all what their own personal goals and motivations were to do this. They ended up going out for drinks after the bottle of wine (I didn’t join) and called me the day after and said that they were separating and closing the company. They had drifted too far apart. They were very happy that they had found out now, and not spent another year and not only wasting time but probably dumping their friendship altogether.