Mid-program reflections #4 – six thoughts about Office Hours

17.20, Friday 20 Apr 2018

I meet with each of the nine startups for an hour every week. The session is called “Office Hours” and I’m pretty sure that all startup accelerators do something like this.

For me, it’s about founder coaching and generally making sure each team is getting the most out of the program.

I first saw how this works because of Jon Bradford. I was lucky enough to sit in on his Office Hours sessions in 2014 when he was MD with Techstars London. I’ve developed my own style since. All the good bits are from Jon.

“MD” stands for “Managing Director.”

What does a program Managing Director do? I can’t tell you in general, but I can say what I do.

I lead on outreach and then selecting the startups. I make the case to the rest of the team about why each startup is worth investment, and I have a thesis about what’s happening in the market. I lead on deal negotiation, and I coordinate the legal team.

Programming: I work closely with the Program Director, Lisa Ritchie, and her program team. In theory I’m backstop if there’s trouble, but there’s been little of that: Lisa both runs a tight ship, and thinks imaginatively ahead of the puck. So I’m consulted only as needed, usually as a startup is being handed off between the different parts of the program. Because of my design consultancy background, I’m a second pair of eyes on the briefs for the agency-led Services phase. I bring in much of the network of experts and advisors, and founders for Founder Stories sessions.

I run Office Hours. I coach the startups when they’re in the room, and evangelise for them outside it.

These reflections are about Office Hours. Although this is the ninth paragraph, it was the final paragraph written. I finished writing this post, read it through, then came back here to give you a warning: there are too many words, and I have that horrible deer-in-the-headlights feeling I sometimes get when doing public speaking that, holy shit, everything I’m saying is obvious and asinine. So I’m going to do what I usually do when that feeling comes on, which is to double down and barrel on.

I estimate that I’ve led or sat in on 250 hours of Office Hours sessions. This doesn’t include advisory sessions or board meetings. I don’t feel that 250 hours is enough to get good at it.

Also: who the hell am I to be giving advice? I’m less successful at the startup game than a lot of the people I meet with, and with the rest that’s only because they’re just getting started. But I’ve seen a lot.

So given I don’t feel particularly good at it, I keep notes of approaches that seem to work. This is something I’ve been doing for a couple of years, on and off: privately journaling at the end of the week about working practice and team dynamics.

Then I come back to the approaches later. I don’t mean to follow them slavishly. Only that, in a session, I try to remain conscious of them rather than reacting in the moment.

Six things I try to keep in mind while I’m running an Office Hours session:

1. Do they know how to run the room?

My first session is about us getting to know each other, and talking about what we can expect from Office Hours. After that, I start by asking a question: what’s one great thing and one challenging thing that’s happened over the last week. (Then we dig into the challenging thing.)

About halfway through the program, I put more of the agenda in the hands of the founders: at the beginning of the meeting I get them to write the agenda up on the whiteboard. This becomes habit pretty quickly. If I’m not clear what a topic is, or what kind of response I’m being asked for, I say.

Much of any founder’s time will be spent meeting advisors and investors. There’s a knack to running the room and getting what you want out of it, while maintaining a feeling of collaboration and conversation. Meetings aren’t just time you spend in a room together. Meetings are an atomic unit of work. They should have purpose and outcomes, although these don’t necessarily need to be stated. There are lots of small ways to make sure attendees don’t drift or feel lost.

Most of the founders I work with already know how to run a room. At which point, reassured, we can go back to chatting.

2. Am I thinking a couple weeks ahead?

We provide a bunch of programming to the startups, and I want to make sure it’s effective.

For example, ahead of “mentor” meetings with experts and advisors, we discuss how to pitch (5 minutes to intro the company, then dig deep into one or two issues. They may have to work to make it useful). During the Services phase, I try to bring up the differences between how agencies work and how startups work, and also how to integrate the deliverables.

Absent anything else, I think ahead to the eventual pitch deck. I’m imagining the slides. If there’s not yet a strong traction slide, I work backwards through sales and then to processes around customer development, and guide the conversation to those topics.

Because of this, I need to have a strong opinion about where the company should go and how it will get there. I spend a lot of my time between Office Hours thinking about this. This isn’t so that I can say there is a “right” or “wrong” answer, it’s so I can have a good understanding of the complexity of what they are taking on. Rather than “correct” or “incorrect,” it’s useful to feel out decision qualities such as “ability to easily iterate” or “here be layers of unconscious assumptions and hope.”

Founders are very convincing people, so I have to watch for where an argument is strong because of good analysis versus mere charisma. Sometimes founders convince even themselves. There’s a knack to jumping between sharing visions of the future and robust self-honesty.

My personal mantra is: strong opinions, weakly held. I have to remember that my view is secondary to what the founder and the team wants. Of course my opinion might be that the founder is missing something, so I have to satisfy myself that their decision is made with a good process. (And sometimes the choice is between two routes and the answer is: do whatever you’re ok waking up at 4am and thinking about for the next 4 to 7 years.)

3. Why hasn’t the founder answered this question already?

These founders are some of the brightest people I’ve met. If anyone has the mindset to tackle any challenge they meet, it’s them.

So when a question is brought to Office Hours, I try to ask myself why the answer is not obvious to the founder. I try not to immediately answer it myself.

(There’s another reason why I shouldn’t leap to answering questions, in that the founder has been closer to and thinking more deeply about their startup than I ever will. In the end, all I really have is a perspective.)

Why might a founder ask a question?

There might be a knowledge, skills, or experience gap. This is possible. I think to myself why they have not worked it out with friends or google. We can figure out an approach together, and what I try to do then is ask smaller questions which will lead the founder to the answer for themselves.

A second possibility is that the higher-level framework has something missing. A question about, say, which product features to highlight on the homepage should be obvious given a validated model of the customer and an understanding of product differentiation. And those should be possible to figure out given their priors: in this case, a process of having a business model hypothesis and testing it by speaking to customers and investors.

So a question from a founder is a chance to dig upwards to these frameworks. Frameworks aren’t axioms. They can and should change, but always deliberately.

The important thing here is not the answer, but the ability to deconstruct the question, to ask it intelligently, and to discuss it. If a question can be treated like this, then it can be worked on by the founder with their team and with their advisors–all people who are much smarter and more experienced than me. A question answered by instinct can’t involve and take the benefit of all the smart people around us.

A third possibility is that the answer is clearly evident, but there is some personal or team resistance to seeing it. A resistance comes about often because the answer implies something undesirable. You’d be surprised how often this happens, or maybe you wouldn’t. If it’s a single founder, some possibilities are that:

  • the answer might imply something that conflicts with the founder’s self-image
  • the answer might reveal an undesirable kind of hard work: it’s preferable to do the all-consuming and intellectual hard work of grinding through product development, versus the emotionally scary work of sales and possible rejection (for example)
  • like all answer, this answer means bringing an idea into reality, which is terrifying: all ideas are perfect; reality is at best mundane and at worst can fail

So in this case, I try to help the founder be clear-eyed about what an answer means.

If it’s a team, these different viewpoints can be embodied in different team members. This is not necessarily a conflict. One member might be not surfacing the answer because they imagine another team member is highly invested in a different approach. Possibilities are unvoiced from an overabundance of care. My job here is to help them become a functional team, and one way to do that is to illustrate the power of saying conflicting viewpoints out loud. So I try to point of differences of opinion. Just because differences of opinion have been unearthed does not mean they need to be resolved. Differences can be tolerated and embraced. (Although courses of action, once decided, need commitment.)

I have a hobby interest in small group dynamics, so I love these sessions intellectually. Though they are the hardest to work.

4. There is often a crisis. Fixing the issue is not my job.

A special type of Office Hours is when there’s a crisis. I would characterise a crisis as any time the founder brings urgency into the room–whether it’s good or bad. There are times when sales are going just too well! “A great problem to have” can trigger a panicked response just as a more existential crisis such as an unhappy team.

I have to remind myself that fixing the issue is not my primary job. Participating in panic validates panic as a response. But if a startup responded to every crisis with panic, nothing would get done. (I would characterise panic as short-termist thinking, accompanied by a stressed and unpleasant emotional state.)

What makes this challenging is that I often know what they’re going through. Sometimes I recognise a situation and my own emotional memories well up. There have been sessions where my heart races, or my palms sweat, or I look from team member to team member and wonder if they realise the dynamic they’ve found themselves in.

So before we talk about the issue, I try to find the appropriate emotional response: enthusiastically cheer first sales (but don’t sit back on laurels); get pissed off about bad news but move on with good humour; treat obstacles with seriousness but don’t over-generalise. It’s a marathon not a sprint, and so on.

Then use the situation to talk tactics and build some habits. I like to encourage:

  1. Writing things down. Startups are not about product, they are about operationalising sales of that product. Operationalising means there is a machine. The minimum viable machine is a google doc with a checklist. The sales process can be a checklist. HR can be a checklist. Bookkeeping can be a checklist. When things don’t work, revise the checklist. Eventually, turn it into software and people following specific job objectives. This is how (a) the startup can scale where revenue scales faster than cost of sale; and (b) the founder can one day take a holiday.
  2. A habit of momentum. I forget who said to me “first we figure out how to row the boat, then we choose the direction” but movement is a team habit. If, in every meeting, i respond to a business update with “so, what are you doing about that” then that expectation of action will eventually get internalised

I find these viewpoints sink in better when they’re using in responding to a crisis.

I also like to encourage self-honesty. Sometimes my job is to say out loud things which are unsaid. Founders are very good at being convincing (both themselves and others) otherwise they wouldn’t be founders. Sometimes that data that doesn’t fit the narrative is left out… to others and to themselves. So I can help break that down.

There will be crises and crises and crises. But we only have these Office Hours for 12 weeks. If we concentrate on fixing just today’s issue, we miss the opportunity to build habits that can handle tomorrow’s.

5. Am I being useful right now?

As much as the above is useful in the long-term, there has to be a balance: these sessions should also tackle the issues brought into the room. In the last few weeks of the program, I find that we spend more and more time on day-to-day business issues. The founders have figured out how to get what they need out of me. And if they can do it with me, my hopes are high they can do it with anyone.

What do we look at? An iteration of the pitch deck. A run-through of the sales process. How to hear a “no” as a description of what a customer wants, and to use it to win the sale. Examples of pipelines and proposals. The agenda for a weekly growth meeting. Showing how the almost identical pitch deck can be re-pitched with added intensity if you pay attention to emotional narrative and rhetoric. Investor motivations.

I’m not an expert, but I do a lot of things a little bit, so I can be a useful second pair of eyes.

(I pay attention when the same topic comes up more than once and try to understand why the founder has not instinctively generalised.)

Also towards the end of the program, I get more open about some of my approaches above. The sessions get more and more collaborative. In the end I’m learning quite a lot.

6. If nothing comes up, getting to know each other is great.

I want to make it very clear that all the good stuff you see is entirely down to the startups themselves. Advice is bullshit. The bar I set myself is: can this hour be more effective than the hour they would otherwise spend building their business. Almost certainly not.

As I said above, the founder has been thinking way more about their company and their market than I have. There are experts out there far smarter than me. But there’s a bigger point:

I have to remind myself it’s not my company. I don’t make the decisions. In the event that I do recommend a direction, I remind myself that I mustn’t get offended if they don’t take my advice. (It’s a natural and human response to be offended when offered office is not taken.) It’s not that I ought not be offended–it’s that being offended would be a category error. The material I work with is the actions of the founder. The material isn’t right or wrong, it simply is.

A good way to do all of the above–to react appropriately, to coach good habits, and to be useful–is for the founder, team, and me to get to know one another. The better you know each other’s values, the higher the information content of any given interaction. So sometimes the best thing to do is to hang out.

Reading these reflections, I sound, even to myself, like a pompous arse. I mean, there’s a very good chance that I am a pompous arse, which would be the reason why.

Honestly mostly the sessions are just chatting. I work hard to make them useful chatting, and yes I probably overthink it. My Office Hours will be more useful to some founders than to others. And I sure a lot of people, in my shoes, would do a much better job and wouldn’t indulge themselves with endless introspection.

Amateur hour coaching, that’s all it is.

This feeling is so strong that I think I will have to warn readers somewhere near the top. Say, around the ninth paragraph.

Here’s a quote from Bob Shaw’s short story “Call me Dumbo,” found in the collection Tomorrow Lies in Ambush.

An aircraft factory is a machine for producing aeroplanes and it may be disastrous to attempt to improve production by piecemeal tinkering with individual departments–one must seek out in all its ramifications, and destroy, the machine for stopping the production of aeroplanes, which lurks like a parasite within the organisation.

I love this way of thinking.

Let’s start from the perspective that a startup is a machine for growing. But there are obstacles which temper the growth. Our job, together, is to identify and to remove the invisible anti-growth machine.

The end of week 10.

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