Years ago I remember I was angrily smushing down the plunger on the office aeropress when my cofounder banged down his empty cup triumphantly beside mine. He shook his head and murmured: “that was such a good meeting…” with a tone of gravitas like it had been this profound spiritual experience and not a hamhanded micromanagement session. I decided not to throw the half extracted coffee in his face but really struggled to encapsulate in a single response why it was not a good meeting. The fact is: the meeting was really good for him, but not for the rest of us… Let me explain…

Feeling heard

We’d been briefed to review our product strategy - but hadn’t really been given the details of how the meeting would be run and what to prepare. Just “Hey guys - please prep for this meeting”. How? What do you need us to look at? The CEO showed up with a full personal agenda that he hadn’t shared that he proceeded to go through. Kicking off: he told us the purpose of the meeting (high level) and that he wants us to collaborate and get involved + give him feedback… Ok.

Next, he approached all of the issues we were having as being something that we could solve by employing some sort of short term strategy. At this point we’d be running 3~ years and we had the same flip/flop levers we could pull on long term strategy. “We should go back to doing x” or “we should run a seasonal campaign for y”. It was all the same stuff. I had the feeling that there were some hot takes at that table but not necessarilly fully formed into something we could collaborate on.

Finally, he encouraged people to pipe up but would cut them off/complete their sentences and scribble down notes before they’d really had the ability to flesh out their ideas. He was asking (verbally) for collaboration but his actions were all about crossing off a few key points on his personal agenda so as to unclutter his mind. It’s not a good leadership style when you’re in a startup scenario that requires creativity from your reports…

Brute force leadership

The first time I came across this concept was when I was working in an accelerator in Dublin years ago. A well intentioned colleague commented on a partnership I had formed saying that “maybe the profile of an aggressive salesperson is not what you’re looking for there”. Now I know what that means… But when I was younger I just saw it as a plus for the business. Why? Salespeople/‘brute force’ types bulldoze through storytelling with prospective investors, get things over the line, lack insecurities and deliver at the start. But these profiles are horrendous at encouraging an almost artistic creative zenlike space for people who have big ideas for the business but don’t necessarily perform well when pressed in quick rapid-fire pitch-like meetings.

Getting a group of different people from different backgrounds to collaborate together and stoke creativity to innovate and come up with unique ideas aligned to a vision you set out: salesman don’t do this. This is a different type of leadership.

The well prepared tech expert and the creative designer share in common the idea that their type of collaboration or communication is usually storytelling. Storytelling is all about: the preamble, connecting the dots and then hammering home a conclusion or key point. Sales, execs and anyone who’s ever said “time is money” care about the conlusion up front… The hot or controversial take unashamedly delivered… Backed up with connecting the dots + the data… Then sprinkling on top the preamble (contextual specifics to a solution). You need to understand this concept if you want to communicate at the exec/director level vs. the day-to-day tactical level. Middle management is tough, side note.

What else went wrong?

Not reading the room

The body language.

The participants looked defeated as we ran through the action points the CEO had formed. I was clenched up with a balled fist have sitting on my chair half ready to get up (or escape from the situation). The super intelligent BA who knew every number had his hands clasped as he looked directly down at the table. The designer who was trying to follow along had her eyebrows perennially raised and was nodding slowly in an sympatheticly as the CEO rattled off the same list of action items. The other founder - the ops guy - had broken a personal slouch record and was almost horizontal in his chair executing a full back bridge with arms folded.

How was he not seeing this????

Focusing on the wrong outcome

It’s probably not a big surprise when I say that the young BA and the head of design moved on to better prospects only months after this meeting. It wasn’t a last straw, it was just more of the same. The reason was that the meeting seemed to have been called purely to unclutter the mind of the CEO. At the end, he felt he had clarity on what to do next. He got to speak. He had the caffeine induced neuron-connecting a-ha moment cliché jigsaw startup annual plan momentum all together and he encountered no resistance. We stared at the floor as he completed his negotiation.

So we’re going to do X Y and Z and from now on we do this - are we aligned?

Yep sure sounds good.

No-one felt brave enough to break the pattern he’d established as the leader at the table and make suggestions. It wasn’t just that this meeting was uncomfortable, we’d established in the past that ideas/suggestions/changes entered into the CEOs ‘dealflow’ mindset and he would begin negotiating. If it was too much of an intellectual challenge to totally rethink something he would argue against it. Ultimately, he had the final say on everything. There was a lack of trust given to the people he’d appointed to handle certain parts of the business… Ultimately, the meeting wasn’t the root issue; it was merely a symptom of a deeper problem plaguing the management of the business.

Pointers

Ask for bad ideas

Are you creating psychological safety not just in the org but in the meeting? This is a big, deep topic (Amy C. Edmondson wrote a book on it) but there’s basic stuff you can implement that’s actually quite fun. Look at it like this:

The people on your team have ideas…

Maybe you’ve accidentally created an environment (by holding the reins too tightly) where people are nervous to speak up and have an idea rejected…

Tip: ask each team member to give you the worst idea they can think of as a creative exercise.

What’s hilarious about this idea is it could actually accidentally work out. Maybe someone’s ‘terrible idea’ is something that’s worth doing!

More than that, you’re giving them an opportunity to simulate being collectively rejected but also making it safe to do so. They have the excuse that it’s a bad idea, it’s fun, it loosens them up. When they go to give you their real idea they’re less stressed out about the potential rejection. Even then, they can fall back to joking/referencing their bad idea. This works because it’s creating an environment of vulnerability. I’d even suggest that the leader offers up their poor idea first but also let it be an actual idea that you implemented in this or another product.

Match the energy of the room

The bulldozing aggressive salesperson took us all off guard that fateful Tuesday at 10am. We simply weren’t prepped. But feeling out the room and matching the energy levels is a good start. Don’t try to whip people up into a motivational frenzy because it’s how you feel… It’s hard to pull off especially considering a good chunk of meetings are remote now. Sign off on what you think would make a successful meeting - you can even go around the room if you’re really out of alignment. What do we need to get done here for us to feel confident about our strategy?

Use your silence to direct the flow of the conversation

I saw this expertly implementing in a group training I did. The person running the workshop would ask for ideas, but with a serious face pause & wait. He’d ask an open question… wide… Then wait.

…

…

And wait…

10 seconds is a lifetime. 20 is infinity. Someone wouldn’t be able to bear it and they’d pipe up.

I started copying this in my meetings. I wanted everyone attending to feel they owned a part of the strategy. If what’s proposed is a summary of our collective thoughts then each person owns a part of the strategy. I’d wait. And wait. And wait. The same voices would pipe up again and again. When they did I’d say “thanks so much I think that’s a good point, summarise it and let it go dead.” When I’d ask another open question I’d preface it by saying “and thanks again X and Y for being so vocal but let’s hear from another voice on this one…”

If it’s not implemented subtly it can be a bit forceful. But is one way of getting the result you want. Collaboration and collective ownership… NOT ticking your own personal todo list.

In the end…

Getting this right is not just a badge of honour for the leadership in a company… The very success of a startup relying on your ability to get this right. You’re in a race against time and using by the book strategies like trying to Eric Ries your way to success with ABs + product analytics in a fast moving world just won’t do. You need something else. You need the 1+1=3 effect that comes in organisations that are more than the sum of their parts. The ones that thrive on collaboration and invent off the wall brand new creative ideas instead of iterate on old systems hoping maybe to get snapped up by a giant.