How I work with my senior team, and hold them accountable for goals

Identifying my own weaknesses has helped unlock a way to work with my senior team

Preamble: identifying my management weaknesses

Earlier this year (2020) I began working with my executive coach, Hanna. We had raised some additional capital to grow the Lingumi team, and to hire a small group of more senior managers to develop and run parts of the business. I realised how rate-limiting I could be to that team’s ability to execute if I didn’t keep ‘levelling up’ - I’ve never done this bit of company building before.

Hanna ran a 360 on me with several of my colleagues. Our process, and my learnings from it so far, will be the topic of a future newsletter, but (…spoiler alert!) one of the themes that emerged very clearly was that I was not good at holding my team members accountable for clear goals.

The business had clear KPIs and targets, for which we collectively held ourselves accountable, and to which I held myself accountable before the board and our investors. But at the individual level, I wasn’t holding my direct reports individually accountable for specific goals and projects with clear deadlines.

This is a serious (but fixable) weakness, and is very unhelpful to my team. To remind myself of the obvious: ambitious, talented people love having big, clear goals, loads of honest feedback, and feeling like they’re growing and taking on challenges. I love having those things myself.

I’m a fairly non-confrontational person. Perhaps the reason I hold myself accountable for goals, but am bad at doing the same to others, is me subconsciously thinking “I’d have to confront the person if and when they miss a goal”, and avoiding that by setting woolly goals or vague expectations. There’s a melange of other influences here, including being a natural ‘do-er’ and enjoying being ‘in the trenches’, a fairly weak delegator, and having no experience prior to Lingumi of managing a team. These are all very normal things for young managers. Once identified, it’s something an exec coach can help pro-actively develop.

My avoidance of setting clear goals and expectations for my senior team was hurting them, hurting the company, and hurting my own development as a leader and manager. So, we began work on fixing it!

In my coach Hanna’s own words:

“We saw a need for Toby to move out of ’the trenches’ and lead more from the front; to become more of a task giver than a task taker (he is not the only start up founder who struggles with this as the organization grows!). We looked at both the emotional and practical reasons why this was difficult for Toby to do, and developed a simple way for Toby to more easily follow up and hold others accountable.”

That simple way to follow up, and hold my team accountable, is what I’ll describe below.

My operating rhythm with my team

Before jumping into how I hold my team accountable, I thought it’d be worth discussing our current operating rhythm as a team. I’m very keen to hear alternative working rhythms here — please do hit ‘reply’ if you’ve built up a senior team and have found a good working rhythm with them that’s notably different.

I have three key weekly events with my team:

  1. Weekly SMT meeting: Thursday morning senior team meeting that we either use for a specific topic discussion (eg critiquing the fundraising deck, discussing quarterly or annual strategy), or, more typically, to run a ‘lean coffee’ (hat tip to our CTO, Aaron, for the format) where we post discussion topics on a board, vote on the most pressing ones, and spend 7-8 mins discussing the top issues and deriving actions and who is responsible for them.

  2. Weekly operating meeting(s): with some, but not all, of my team, I have a 30 minute operating meeting each Wednesday to go through ‘BAU’ (business as usual) topics, clearing time for our….

  3. …Weekly checkin / one-on-one: I spend 30-60 mins with each member of my team discussing how they’re doing, their goals, their team’s development, and any major topics arising that they want to discuss.

The system below is something I use before, during, and outside of these meetings.

My team accountability system

The goal of this system is to:

  1. Give me a bird’s eye view on what my senior team are working on, and when we’ll next follow it up or they’ll complete it

  2. Help me to make my expectations for each team member explicit, both to me and them

  3. Be a forcing function - make it really easy for me to hold my team accountable to both of the above

Hanna’s suggestion was ‘a one-pager for each team member that you keep in front of you during every meeting, and constantly update’. My team don’t edit this themselves: it is a private page that I use to help me improve on the areas of weakness outlined above.

I didn’t re-invent the wheel when implementing this. Mine is in Notion, because we use it a lot internally, but it could be a spreadsheet, or a Trello board, or something else. I recommend something that gives a Kanban view.

One caveat here is that this is a very rough v0.1 of this system, so no doubt it will change, and I’d be curious to hear of other approaches. I wanted to share early, because that’s in the spirit of this newsletter - I’m learning as I go. My sense is that most managers are much more ad-hoc or ‘it’s in my head’ about this. That might work fine for you.

So, here’s what I now see in my ‘My Team’ page in Notion:

The key parts are: easy shortcuts to each of my team’s pages, easy access to some of my own key pages, and a view of my own ‘big things’.

Inside each team member’s page, I see their version of this ‘bird’s eye view’ board, and my expectations for them, written out nice and clearly. Here’s my page for Rich, our Head of Product, as an example.

I’ve hidden the exact expectations here, but they emerge from areas of development that I identify for each person in my team. Do they keep pushing back deadlines? I’ll put ‘meeting agreed deadlines, even if it’s just a rough draft’ or ‘prioritising time to focus on deadlines on key work’ or similar. Do they respond poorly to feedback? I’ll go for ‘asking for feedback regularly, and handling tough feedback calmly and positively’. It’s that sort of thing.

So here’s my second caveat: this system is simply a forcing function for me to improve my approach to accountability. My memory of much of these things is fine, but the saying ‘out of sight, out of mind’ applies: if I can see it, and see the dates, I feel I can keep pushing myself to ask my team for clear commitments, clear dates, and assessing their progress against expectations.

If I were naturally really strong on expectation setting and deadlines, I may not need this, but would need a ‘one-pager’ that is tailored to whatever other weaknesses I had.

The process Hanna and I have created naturally works with my weaknesses, and even converts them to strengths; I often screen-share my board view during one-on-ones, collaboratively date-setting and expectation-checking, which means it becomes a friendly, shared experience, rather than an obligation I feel I have to carry out alone.

Pros and Cons

I’ve only been using this system for a couple of months, but I think it has enormously improved my process of working with my team, and has certainly helped me to hold them, and myself, accountable to clear goals and timelines.

The hardest part so far has been codifying expectations. Expectations are behavioural; identifying an area of development for a very experienced, intelligent, hard-working operator can be challenging. A simple Notion board won’t fix that. The struggle, as I recently expressed it to one of my team, is that for long periods, it feels (reassuringly) like they’re operating at their A-game…what can I point out to improve?

Hanna and I talked this one over. We discussed three routes:

  1. Ask the team member, “it feels to me like you’re on your A-game, how does it feel to you? What’s missing to get you there?” - often something unexpected emerges that I can work on with them. Highly self-aware individuals hold themselves accountable for weaknesses that I’ve not identified.

  2. Ask myself “what am I having to think about or facilitate in the business, that this person could be doing instead?” — often I’m working on something, and enjoying doing it, but as a result, am failing to see that this is something that a team member could, and should, be doing. I’m not a good delegator, so this is a helpful one for me.

  3. Meeting the best in the field (or some later-stage CEOs) to discuss ‘what exceptional looks like’ in a given position at the next stage. In some cases, matching my team member to someone great one or two steps ahead for mentoring. I haven’t done much of this so far.

The second point in particular has been on my mind a lot recently. Using that question, I realised that a member of my team had been executing a very tactical, short-term strategy fantastically, but hadn’t carved out enough time for longer-term strategic planning for their team/dept.

I brought it up with them in a checkin, and we discussed how - and if - they should prioritise differently to create the headspace for it. The next step will be to hold them accountable for some output there. We agreed on how they’d do that, and when we’d next meet to discuss the resulting work.

This felt like a major step forward for me on one of my weak spots: identifying an area of development for someone in my team, raising it as an expectation, and making it an action item for which I will hold them accountable. If you’re anything like me, you’ll recognise how hard that cycle can be. For others, this will sound like second nature work. I’m just delighted to have identified a key weakness, and begun improving against it.

That’s all for this month! I don’t know what I’ll write about next. I have a backlog of ideas, but I’m open to other topics if you’re pondering something. Hit ‘reply’. Thanks to those who emailed in response to my last pieces - I’ve enjoyed the feedback and discussions.