Deep Dizzying Difficult Determined Discussions

Imagine 5 people whose opinions/advice you value/respect. They can be past teachers, past mentors, various important people or famous people you’ve met. (This works better if you actually take some time to do it so here’s a picture for you while you think.)

Me with a bag, somewhere in SF, under heavy attack from the wind.

Alright, now that you have your 5 people, imagine convening them for 1 hour. The purpose of the hour is to talk about your life — updating them on what you’ve been up to and figuring out what you should do next. How would you plan the discussion?

Yesterday morning, this is roughly the question we asked ourselves with a board meeting looming in the afternoon. We ended up deciding to spend the first half of the meeting n introductions and an overview of our recent work. The second half was dedicated to a couple discussion questions:

  • What are our blind spots?
  • What are exciting/new ideas we could bring to Demo Day?*

Just like you would for any ESP discussion, we started asking ourselves questions like what’s the value of convening all these great minds? how should we structure the discussion to get the most out of it? what actionable decisions do we want to be able to make coming out of the discussion?

Our prep mostly surrounded what question topics would be the most useful to ask about and would there be enough time for 2? 3? 4? questions? Coming out of the discussion, we realized this prep wasn’t enough. The discussion was very low energy — board members didn’t feel too comfortable opening up and giving honest feedback. The questions were much too vague (as I’m sure many of you can tell). Most of the blind spots weren’t actually blindspots. Some of them weren’t even weaknesses? So clearly people didn’t even understand the point of the question. Finally, the energy never seemed to hit a peak (you know like 1.5 hours into the morning retreat discussion when you’ve gone too far) — at the end of the meeting, it felt like peoples’ minds were still warming up.

Today, we got to have even more discussions! (For those that don’t know me, I love discussions!) We talked to two strategic advisors with experience in their own non-profits and advising many other non-profits basically for the entire day. The discussion was kinda loosely organized — we mostly just talked about anything with a little bit of structure in between.

We started with meditation and relationship building. I think more than ever, I saw how important intentional relationship building can be to the success of a discussion. If people are not willing to be honest and vulnerable, it’s almost impossible to have a meaningful discussion (particularly if the topics are very personal / emotional ones).

Next, we gave program updates. The two advisors (omitting names for privacy) asked lots and lots of questions. Whenever we’d explain some part of Project Invent, they’d ask questions until they understood exactly why we were doing some thing, how successful our actions were toward that goal, and what assumptions we were making in our answers. Maybe surprisingly, I think they had very different life opinions/assumptions than us, leading to lots of identified potential assumption mistakes (or maybe they’re just really great at identifying assumptions outside of their own views on life). Asking these questions really did two things. First, it meant that for all future conversation, we’d be on the same page. Second, and maybe more useful, asking the hard questions really poked at all the soft spots we’ve been ignoring or avoiding.

After this, we moved into a SWOC analysis. I think it’s unclear to me how thinking about this mentally translates into actionable decisions, but at the very least, this did generate lots of ideas and talking points — from improving at fundraising to defining goals for teams after one year in Project Invent.

By the end of the day, we were both exhausted but somewhat energized by all the ideas. Next, we’ll have to synthesize all the thoughts and reflect on the points made that we truly believe are important and worth working on / thinking about.

I think after these two days of strategy discussions, here are some of my realizations about discussions:

Discussions are how real decisions are made. I feel like this is something I’ve always vaguely known / been aware of. Maybe it’s one of those things where if someone else told me this I’d be like “yeah, ok. sounds reasonable. so what?” I guess my three takeaways from these last two days are really

  1. I wish I could be in on these types of discussions. It seems like a really important way to make an impact. Discussion / negotiation / persuasion skill directly translates to decisions (if done well)
  2. If I were ever to have my own board to make decisions, it’s really important that I surround myself with people I trust to have a good, productive discussions — and I think it’s really hard to find people like this.
  3. These discussions sound like so much fun!

Problems with discussion productivity seem to continue existing outside of ESP discussions. Though the two strategic advisors had extremely interesting ideas, sometimes we struggled with keeping the discussion oriented. So, even if these peoples’ jobs are to have these discussions effectively, this doesn’t mean they necessarily think in an organized way. This then means it’s really important to keep discussions in check and that good facilitators are very valuable people.

I’ll end this post here. Here are a few more fun pictures from the last few days:

Ramen Nagi. I waited for over an hour with Jerry and Aofei (!!!) for this ramen. Was worth the wait.
3 super cheap pastries/bread things I got for $2.50 at a Mexican bakery. Lasted 2 meals.
Tasty Hot Pot in Santa Clara. Personal hot pot bowl — very fancy and pretty good.



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