Tell me your leadership tricks and tips
Most of us want to be better at things. One of the things I want to be better at is leadership. I’d like to be better both in an abstract “I like learning and improving” kind of a way and also in a “it’s kind of my job and would probably make me more effective” kind of a way.
I decided to write this out for two reasons:
- I’d like to hear your tips and habits — what do you do that helps you be more effective at getting groups of people pulling in the same direction, achieving group goals etc?
- I’m trying some new things, and I thought that if I wrote them out, I’d both think about them more deeply and also add a bit of accountability when I come back and see how much stuck
Things I’ve done for a while
I’ve written a bit about personal productivity before and as I look back at it, there’s a bunch of overlap between what I thought and wrote about productivity and the day-to-day of leadership: avoiding being a bottleneck, keeping track of open loops and delegated tasks to hold people accountable, and trying to work on the right things. Some of the things in that post have stuck, and I still do them ~8.5 years later, but even the things that have changed over the years benefited from writing them out, I think.
Since publishing that post, we have started using 15five which I find really helps me with the weekly review cadence but re-reading it also reminds me that I’ve been less good recently at explicit daily reviews, and at systematically keeping track of open loops to follow up with people about.
Keep a list of things to discuss with each direct report
I believe pretty strongly in giving the team as much autonomy as possible, and part of that is staying out of their way. To that end, I do a few things to try to be mindful of their time and productivity. One of the best tips I’ve received which applies not only to managers but also to peers and managees as well:
Keep a list of things you want to talk to each collaborator about. Whenever something non-urgent comes up, add it to the list instead of interrupting them to discuss it immediately.
I keep this in one long Trello list, starting each card with the person’s name for easy filtering. For my direct reports, I review my list of things to discuss in our weekly 1:1s.
Have weekly 1:1s with each direct report
Speaking of 1:1s, my only weekly meetings are:
- Weekly 1:1s with each of my direct reports (mainly their meeting but reviewing my list as well)
- Weekly team meeting with the leadership team (relatively unstructured catch-up since we aren’t colocated)
I’ve tended to schedule the more strategic meetings (quarterly / annual planning and the like) in a more ad hoc way, but I’d like to be better about the repeated cadence of those.
The key to a good one-on-one meeting is the understanding that it is the employee’s meeting rather than the manager’s meeting. This is the free-form meeting for all the pressing issues, brilliant ideas, and chronic frustrations that do not fit neatly into status reports, email, and other less personal and intimate mechanisms.
Work off a short list of focused priorities that is separate to your todo list
More related to personal productivity, I found it was transformational a few years ago when I stopped working off a todo list. I still have a backlog where I dump things I want to do, and have time-based alerts and reminders for specific things that have to be done on certain days (and of course calendar entries for specific time slots), but I try not to pick a thing to work on by just turning to the never-ending todo list and picking something. Instead:
Select things off the list in a more mindful way and have a very short list of things to do each day and each week
Have internal and external opinions
Everyone has their own style, but I personally find it good for me and good for the team if I stay abreast of changes in our ever-evolving industry, and have opinions on the trends.
As a result I write and talk a fair bit about the future: the future of the big technology players, the future of the industry itself, and the future of user behaviour (and what it’s not).
I think that this helps me make better decisions, but also helps align the company, gives my colleagues information to share with clients and prospects, and bolsters confidence in our shared direction.
Interestingly, I also find that some of my most productive days are when I do a similar thing internally:
My best days involve hammering out first drafts of things and / or “editorial” review and oversight of others’ drafts.
I think there’s a certain kind of leadership role that looks a lot like being an editor.
Things I’m trying to start doing
I like thinking about self-improvement at this time of year so I can pretend I’m not making new year’s resolutions which I have a kind of in-built aversion to. I’d rather pretend I’m doing this stuff because I want to rather than because it’s a date when society tells us to focus on self-improvement.
Get better at trying new things with an explicit plan for stopping if they don’t work
I’ve found myself saying (often to myself) a lot recently:
If you want to get something different, do something different.
So: I’m trying to hold myself accountable to figure out the areas where I want something different to happen and ensure that I’m going to do something different in that area of life / work.
But I recognise that two of my weaknesses converge in this area to make me struggle:
- I often have a status quo bias and a tendency to lean towards incremental change that I need to fight to make decisive changes
- I need to be better at having the discipline to review the portfolio of “new things” on a regular schedule and shut down / change the experiments that aren’t working
Apart from talking to my team to bolster my weaknesses in this area and hold me to account, I’ve also started a “decision log” where I’m trying to track all the significant decisions I make so that I can both hold myself to account and get a feedback loop to teach myself that quick decisions are generally better than no decisions.
Connect our objectives together better
We have run a quarterly OKR process for years, but I want to get better at:
- Connecting the quarterly objectives up to longer-term goals
- Telling the story of how our objectives connect to the underlying “why” we’re doing the things we’re doing
In order to make them truly effective, I also want to improve my “administration” of the objectives and goals process. I don’t find it naturally easy to have frequent and regular review processes, but this is an area where I recognise their value.
One really tactical thing I want to improve in this area is the weekly email I send to the whole company. It’s been / has become very focused on news (client wins and losses, new hires, significant milestones etc) but I’d like to get better at both storytelling and joining the dots from today’s news to overall performance.
Communicate better
While I occasionally daydream about running a company that can all get together in one place easily, or at least is on the same freaking timezone, that’s not the one we have. Running even a small leadership team that is separated by 8 hours of timezones and nearly 5,000 miles is hard enough, but having the whole company spread out the same way adds challenges.
There are simple things that help that we nevertheless found difficult to do continuously. We recently picked back up with regular all-hands meetings after they became a little stale and lapsed. A new format, and regularity without extreme frequency (we’ve restarted them quarterly) should hopefully help.
I feel that a simple cadence of structured communications should help here, but I find it really hard to maintain the rhythm:
Weekly: status update email
Monthly: metrics and performance
Quarterly: all-hands, OKR comms and retrospective
The need to get better at company-wide comms is probably the biggest recurring theme of feedback I’ve had over the years at Distilled, which is why so much of this is focused on that area.
Things I’ve seen others do that I’d like to be better at
One of the downsides of running your own company is that you tend to end up doing it for a long time and so you don’t get as much exposure to different management styles and others’ ways of doing things. Because I don’t get to go and work for a different boss, I have to extrapolate from public and semi-public hints of great things other people do (and that’s one of my reasons for writing this post).
But. Some things I have seen that I’d love to emulate:
Write. Just write. For an internal audience
Most of my writing is either for an external audience, or is relatively formulaic and structured. For an internal audience, I write status updates, I write objectives, and I write pitches and business cases, but I don’t write things that look like blog posts that are only to be shared with the team.
A founder friend of mine told me how he spends a couple of hours a week, typically first thing on a Monday morning, writing. Just writing for his team:
Every Monday I write an essay for the company on some topic that I feel is pertinent to the whole organization.
I think I can get better at this because I can see the white space that gets left between my public writing (which might have personality but doesn’t contain secrets) and too much of my private writing (which can tend to the formulaic).
I’d like to learn to fill that gap with more open discussion of challenges and opportunities we face to avoid what my colleague Tom Capper described as:
…open secrets, discussed in hushed tones…
Shining a light on the “open secrets” and discussing them more widely should help us dig out conflict and get aligned.
Decide already
I’m lucky to be surrounded by leadership team colleagues who are better at this than I am and who push me to be better.
It’s important to make good decisions. But I spend much less time and energy worrying about “making the right decision” and much more time and energy ensuring that any decision I make turns out right.
— Scott McNealy, Sun Microsystems via my colleague Craig’s SearchLove talk
Jess, who runs our London team, is particularly good at both showing what this looks like in practice and at pushing me to improve here.
Routines can be a good thing when it comes to metrics and performance
Back in 2011, we made a small angel investment in a startup called Server Density (which merged with StackPath earlier this year). One of the things I always loved as an investor was the regularity with which the founder, David Mytton sent out metrics and status updates. He ran a diligent personal process to review metrics at the beginning of every month and sent his update out on or close to the first of each month.
He was (and no doubt still is) exceptionally good at choosing a standard format that conveyed a lot of information very efficiently and then reporting in that format regularly and in a timely fashion along with less structured, more freeform information to put the metrics in context. He did this through good times and bad, for himself, his investors and his wider team, and with a diligence that I definitely aspire to.
He covered some of his thinking behind the updates in his post on startup board meetings:
You can’t have a proper discussion if the participants do not have the same level of knowledge… The best decisions happen when everyone if sufficiently informed to have a debate about the issue at hand and be able to effectively advocate for their point of view.
My call for ideas and support
I said that one of my big reasons for writing this was to get your input. What do you do? What have you seen others do?
- If you know me, tell me what you’d like to see me do specifically
- Tell me your favourite leadership habits and behaviours
- Tell me the best habits and behaviours you have observed in others
Thank you. I hope something I’ve written here is helpful to you in return.
