Strategic technology leader. CTO at Kooth, a company specialising in digital mental health. Previously Technical Director at the Financial Times, Technical Architect at the Government Digital Service.
I recently read Scaling People by Claire Hughes Johnson, former COO of Stripe. I was first interested in it because it was reviewed in the Economist (paywall) and then an excellent colleague of mine recommended it. Here are my notes.
It’s about 500 pages, hardcover and structured like a textbook. My colleague Aaron Lawlor suggested the format may be because it is aimed at the business school market.
Having read it, I can imagine there are some bits I might want to refer back to, but overall, it didn’t completely work for me. However there were quite a few interesting parts.
“No matter how brilliant a company is, it will not get far, let alone have an impact at scale, without strong management and sound operating systems”. She then she gives guidance on what these might look like.
They start with what she calls “Essential operating principles”, which are the guidelines you use to make decisions and get things done.
Her four are:
The rest of the book is based on these principles and the “operating system:, i.e. the core processes that she has built around them.
She acknowledges that your core principles will likely be different. Her position is that you need to work out what yours are in order to drive the operating principles of a company.
Your core principles may not be immediately apparent to you. A good way to start is by working out your most important values. She includes an extract in the book from a values exercise you can do online (PDF).
There is an extra step which I could have used a bit more detail on: getting from your core principles to the values of a company where others’ core principles will be different.
This is one of her core principles. There was an interesting thought that has stayed with me:
Throughout the book she comes back to this principle, for example around feedback, building trust etc.
The books is really focused on the tools and examples that she built up at Stripe and there is a lot of documentation included.
One really interesting one is the Stripe values document. It’s long, a lot longer than a usual values document, and really paints a picture of what it’s like to work at Stripe.
For me, it made it very clear that it isn’t somewhere I’d want to work, which in itself is useful and does more than a usual values statement does.
One of her takes on the difference between leadership and management is: “Once you become a great manager, you can get very comfortable. But once you become a true leader, almost every day is uncomfortable.”
“A strategy should hurt”. It should be painful and disappointing, either internally or to your customers. There’s no such thing as a strong strategy that prioritises everything at once.
A key role of leadership is to invest in critical work that no one else will naturally step up to prioritise.
The book includes a large extract from this blog post on good goals by a former product leader at Stripe. The post is worth reading in full.
She also makes some concrete suggestions around the cadence of reviews, for example quarterly business reviews.
I also recently read an interesting post on LinkedIn extolling the virtues of shortening the planning process. For me, the really compelling point there was “because it was so short, it actually also ALLOWED everyone to focus 100% on planning and delay their other work” which is something I and my engineering leadership team have experienced a bit of recently.
This all together has some good, well-thought out ideas on how to run a planning process that works well.
She has some great insight into how to improve recruitment. The process doesn’t end with the hire, but with a successful onboarding and a strong connection between the new hire and their company overall.
She talks about getting recognised in a tough market. There are usual ways, like writing blog posts, but Stripe went a lot further than that. They held several capture the flag competitions which created a strong talent brand and drove leads to the hiring process.
She includes a write-up of the work involved to set that up, and it was a lot. Several weeks, many engineers, a residential week for the core team of engineers in North Dakota for the crunch period. It was a major piece of work, and she doesn’t really dwell on that point. It’s an interesting thought experiment about just how important you think it is to hire the best.
Be really clear about the work environment and watch out for language that subtly transmits bias – use tools like Textio to check that.
Make your job ads genuine, not a rosy ad. Be self aware as a company. Knowing who you are helps you hire well.
Think about who is successful at the company. What qualities do they share and what questions can you ask to suss out whether candidates have those qualities?
She also has some great background on how Stripe makes it clear that hiring is everyone’s job. They have some clear principles for all involved: hiring managers, interviews and recruitment, about how to make hiring successful. For example, keep calendar accurate, reply to any candidate question within 48 hours or send on to hiring manager; and on recruitment’s side, be respectful of calendars, shepherd candidates through offsites, etc.
Her advice is that the founder should meet each hire until the the company is about 100 people, because they are the people critical to the company’s trajectory.
She advocates really spending a lot of time on hiring. Talent is everything. Hiring is expensive but it is a critical foundation.
It’s good to ask then how their colleagues would describe them and about constructive feedback they’ve received. (I’ve also been asked: how would your reports describe you).
Always make reference calls; at least one reference call should be made by the hiring manager themselves. One question she likes to ask: “Is this person in the top 50 per cent of people you’ve worked with?” Then “top 20? 10, 5?” She says people can be positive, but will usually be honest when asked for data. “If someone only says the candidate is in the top 20 percent of folks they’ve worked with, that’s not a ringing reference.”
She also has some other questions like, where do you see them in three years, when was the last time you didn’t see eye to eye, and what advice do you have for me as a manager as to how I can best support them, which gives insight into their weakness/development areas. This is useful for the hire decision, but is also useful for starting to work with them.
Screen the candidate so that at least two important people are excited by them. Bring in the main stakeholders, even those you think will be negative. Make sure hiring deliberation is a feedback forum not a decision-making forum.
She also stresses the importance of the announcement, which should remind people of the process, celebrate the person you’ve hired and explain why they are right for the company and the role.
It’s key when hiring senior people that you dig into their answers, to make sure they are not just giving you a pre-prepared answer that won’t suit your context. Senior people will be good at interviewing.
This was a section I felt I may refer back to, or pass on to others. A lot of detail on how to onboard, including the “why” of the company and the “how” of company behaviours.
She says company leadership should take part in onboarding, possibly a monthly session where leaders talk about values etc.
If a hiring mistake is made, do a retrospective on your process.
Interesting ideas about processes to track things like internal mobility. Are people moving for career growth, or does it say something about a certain manager or team?
Performance tools are focused on the individual, but it’s teams that get the work done. Investment in teams is not something you can finish; “team development is more like a set of habits you cultivate over time, some performed by the manager and some by team members.”
We should all be learning how to teach and facilitate change management.
At first your work is about building a common team understanding of the type of team you want to be and of the results you want to achieve.
If you are thinking about restructuring a team, she recommends mapping out the structure best suited to accomplish your team’s goals and then write out how you’d communicate it – the narrative about why this is the best structure to support your strategy. Similar to writing a press release before you’ve finished a product, writing a comms plan at this point can expose gaps in your thinking and surface potential objections.
She has some good examples of where you might be under-delegating or over-delegating to your team.
Under-delegating: you are involved in all the team’s work, you ask to review it all before seen externally. Some clues you may be under-delegating:
Over-delegating: you are good at making employees feel empowered and trusted but you are too far away from the work and may also give people work they are not ready for. Some clues you may be over-delegating:
I definitely recognised one or two of the over-delegating examples she gave – sorry previous teams!
When delegating, explain why the work is right for the person, e.g. with reference to their development goals.
Structure, agendas, prep, etc. She has given a talk about it.
One new idea to me was checking out. I’ve written before about meeting check-ins. We recently did some team training where they said “you haven’t joined a meeting until you’ve spoken” and suggested check-ins for every meeting.
Hughes Johnson’s suggestion is start with maybe just one word on how you are feeling, and then also end the meeting with a checkout, for example, are you happy with the decision we took?
In a larger company, do data analysis, for example average designations for a given group, or promotion percentages between employees of different genders, or remote and non-remote employees.
In a smaller company, a more manual calibation: submit scores ahead of time and look for anomalies. Over time, these meetings become less about reviewing each person in detail and more about gut-checking what each designation means, and finding examples so that every manager can calibrate to what, for example, “meets expectations” means for a certain role and level.
It is important to remind people of the kind of cognitive biases that might surface: beyond unconscious bias, she mentions availability, recency and confirmation biases as examples. Understand and coach the group on how to avoid each one.
Her suggestion of how to actually do the calibration is similar to the process we used when I was at the Government Digital Service. Start at the more junior levels with everyone in the room, and once you start reviewing people who are at the same level as the managers in the room, start excusing the more junior managers.
Do a final review of the data afterwards to check for broad parity. Then roll up to senior leadership to review and check for an expected distribution. It shouldn’t be a forced distribution, but high n counts should have a roughly normal distribution. Senior management should also review that the percentage of employees being promoted feels equitable and in line with compensation budgets.
She divides high performers into ‘pushers’, who are highly ambitious, can be very critical, set high standards for themselves and others, and are internally motivated, and ‘pullers’, who take on much more work than they should and deliver high-quality output, but they get burned out; they are more externally motivated and have trouble saying no.
She then suggests some ways you can motivate and develop these two kinds of performers.
Pushers: encourage and reward them for the high standards they set; ask them to lead projects to address areas that need attention; frame work as development opportunities; coach them on how to exert influence indirectly.
Pullers: help them prioritise and set boundaries; encourage and reward them in private and publically; before they take work on encourage them to ask themseves: am I the most qualified person to do this? Is this the most important thing I could be doing? What would I have to let go in order to do this? Coach them on how to say no.
Aniticipate when the work will become boring and work with your reports to think about where they might want to focus in six months. Include them in your succession planning. Think laterally about opportunities that might give them a chance to grow in the ways they want to, even if they aren’t their logical next step.
Finally, let go. If you can’t find interesting opportunites for a high performer on your team, don’t hold onto them for too long – land them a job in another part of the organisation, or open up your network and help them get another job; play the long game, you’ll have earned their loyalty and trust.
She also suggests pre-exit interviews – ask people: if you were going to leave, what would be the reason? Ask 3-5 people, or maybe the top 10% of talent.
Don’t just spend time with your high performers, also think about people who are not currently high performers but have a lot of potential. She says she obsessess over how to unlock the upside.
For example, someone who always has a completely different perspective on a problem can sometimes feel very disruptive, but they can also engineer the breakthrough the team are seeking. She gives an example of when she was at Google. Someone kept suggesting peer-to-peer support as a solution to their customer support backlog. Eventually she told them “find an external example and write up a way for us to test the concept”. The test was very successful, users were getting help immediately, and it led to a building a new support approach that is still in use.
Finally, she notes medium performers are sources of stability and are often culture carriers. This ties into something we talked about on my IoD leadership course (yet to be written up!) that the ‘medium’ performers, who are competent, consistent, and productive, but aren’t your highest performers, are actually the pillars of the company.
She also goes into a lot of detail about managing poor performers.
One of the things she does in this book is suggest different ways to say things:
I found this a bit grating, and there was a lot of it in the section on managing poor performance. This could be useful for people who don’t have experience here or want advice on exactly what words to use, but it didn’t work for me.
One thing to note is that the content on managing out is definitely not useful if you are not based in the US.
This book contained a lot of great ideas and pulled together a lot of useful resources, but as a whole, I found it tiring, rather than inspiring. I am not sure if that was the style, or just that I am not the target audience. It was definitely management rather than leadership.
It’s also very long. Hughes Johnson says it’s not necessarily to be read cover-to-cover but instead pick it up and go to the page of what’s on your mind. However, for that to be the case, the contents pages and index need to be a lot better.
If you are in a company that doesn’t have good processes, particularly around people management, then this definitely has a lot of useful content and good ideas, but it wasn’t a strong recommend from me.
In June, I delivered a talk at Turing Fest on how to create a strategy. Here is the video, the slides and a short write-up.
When I first starting working on strategy, the question I had was ‘how do you actually do it?’. Since then, having read a lot, been on some courses and practiced a lot, I now have a better idea; and the purpose of this talk was to share what I myself would have wanted to know when starting out.
In the talk, I go through some specific models, with examples.
These tools, techniques and actionable advice will set you up to be able to create and deliver an effective strategy.
You can watch the talk here:
And the slides are here:
Earlier this year, I keynoted the second day of CTO Craft Con: The Strategic CTO, and the video is now available:
You can also read more about the discussion in my write-up.
I was in conversation with the excellent Emma Hopkinson-Spark.
Emma kicked it off by asking what strategy actually is, and how it’s different from roadmaps, initiatives, tactics etc. That gave me an opportunity to define strategy as diagnosis, vision and a plan, and recommend the excellent Good Strategy, Bad Strategy.
We talked about communication. The most important aspect of strategy is communication: the point of a strategy is to execute on it, so people need to understand what they need to do.
It needs to be simple enough for people to understand; communication needs to be verbal, visual and written because people absorb information in different ways, and you need to keep repeating it, far more than you might think.
There were also questions from the audience. One was “How do you break out of the delivery whirlwind to set your strategy?” and I was unequivocal on this: as CTO it is your job to set and lead on that strategy, so you have to make time. That could be blocking out time, setting meetings with people to work on it, Away Days, or whatever works for you.
When you make time for strategy, the reactive demands decrease because you have more systemic approaches. I also taked about rocks, pebbles and sand; strategy must be one of the rocks.
It can be really difficult to carve time out to begin with, but once you have, you will start to see the benefits.
Another question was: “what’s the best approach for course correction and how do you tell the difficult story to the board when it’s a drastic change?”
Talking to the board, you should operate on the principle of “no surprises”, so when you see things heading off track, have the conversation as soon as you can.
This led into a discussion how to have that conversation. Emma asked how you change your style if you are communicating upwards, to the board; and one thing I shared was that it’s a good idea to create artefacts (diagrams, documents, progress indicators) and use the same artefacts for everyone: for the board, for your peers, and for your reports, so that everyone knows you are talking about the same thing.
Another question from the audience was “how do you directly incentivise people at all levels around a common strategy?”
This was an interesting question because I don’t think of it like that. Part of the work of strategy is inspiring people with the vision. When you are working on the plan, the more you can involve people, the more bought in they will be.
I don’t think about separately incentivising people, because I find they are motivated by working towards the vision they’ve (hopefully) bought into, with some actions they’ve helped figure out. People like to be involved in delivering something good.
Emma then asked for suggestions on how to actually get started on strategy work.
There were a lot of other great questions, like how OKRs and strategy can work together, aspiring to have an elevator pitch for your strategy, and thinking about strategy mistakes I’ve made.
You can watch the full conversation here.