Book Notes : Scaling People

Tactics for Management and Company Building

It’s been a while since I’ve written one of these book reviews. The truth be told, once I finish a book, if I don’t write these notes up immediately (well within a day or two), I rarely come back to write them. This book has also taken me soo long to finish and complete, that I’m not sure how good these notes will be – however, some notes are better than no notes, so bear with my and I’ll try to do this justice.

Book Summary (in 3 lines)

This book covers the journey of a Box/Google/Stripe leader – and what they have learnt from their roles in these high growth companies. This covers how to setup a foundation (what Claire calls her “operating system”), how to provide feedback (even when its difficult), recruit and manage change. It is a dense book containing a lot of knowledge, and helpfully a lot of conversation and document templates that would be helpful to anyone in a leadership, operational or HR role.

How this book changed me?

As it took me so long to finish its hard to make sure this is complete, but the standouts for me are;

• Goals should be reviewed more often – Quarterly if possible, and you should not be afraid of resetting or changing them if required. Sounds obvious, but this is something I’ve missed in 2023 and looking to change in 2024.
• Leaderships Role – Its leaderships job to make some of the hard decisions and deal with the existential risks of the business. This helped me realise where we were not being strong enough with some internal teams and where we need to step in to help push them in the right direction. Its also our job to coach and act as an unblocker, not do the work for the team under us (so easily forgotten!)
• People management is hard – and always a lot more nuanced than I really give it credit for. I’ll definitely be referring back to this book for advice on how to handle some of the situations and feedback I struggle with.
• The use of “we” and “I” in interviews – I’ve always been tuned to look out for this, but this has helped to build the confidence that I’m correct in how I’ve been seeing this when assessing people. Its important to make sure people can play on a team, but that they were a vital part of the work delivered.
• Simple beats complete – Start something as simple as possible and build from there. I often feel like I need to cover engineer things, instead this has shown me its better to start with something simple, or something off the shelf and build from there than try to engineer the most perfect solution.
• Re-organisation is good – it shows the team is growing in most situations – this is an important frame!
• Finally – I love the idea of an “Engereeication” – I need a reason to role my sleeves up and work on something in the company for a few days a quarter – I think this is what I’ve been missing!

Should you read this book?

If you’re an aspiring manager and leader, absolutely, but make sure you have the time and the space to read it completely. It took me months to finish this book (and multiple plane journeys) to have the time to get through it and digest it completely.

Top 3 Quotes

You’re asked to fly a very complicated aircraft, but you never get time in the practice simulator.

I think this quote neatly summarises how difficult it is to become a manager. This is no simulator, especially in high growth and fast moving industries (e.g. tech)

A side note related to existential risks: A key role of your leadership team should be to invest in critical work that no one else will naturally step up to prioritize.

This quote helped me realise how important it is we play an active role – especially when in times of “war” such as recession or an industry downturn.

“engineerication,” and it’s exactly what it sounds like: He blocks time on his calendar as if he’s on vacation, but instead he spends three to five days acting as an engineer on a team within the company.

I just love this because its exactly what I’ve been thinking and feeling for a while – and will be something I hope to implement in 2024.

Summary and Notes

Goal Setting

Have quarterly goals that you track together.

Sounds simple – but so easily forgotten. I was doing these per year!

the reviews require a lot of effort or feel like they need to be done more often, then your team probably hasn’t fully internalized the goals and isn’t using them to guide day-to-day activities.

This helped me realise how important it is to stay aligned and focused on the right goals as a team to drive our day to day activities.

An individual’s goals should include one or two personal goals

Individuals, as well as managers, should always include personal goals, this allows all of us to develop new abilities to allow them to drive more impact in their role in the future – not just now.

Leaderships Role

A side note related to existential risks: A key role of your leadership team should be to invest in critical work that no one else will naturally step up to prioritize.

I call this out above – but this just shows how important is it to not operate on autopilot and sometimes make the hard decisions teams are missing, either because their in the weeds, or because they want to take the easy route.

But the hardest lesson I’ve had to learn [is that] you get to that point where it’s impossible for you to be successful without trusting others to do things better. And that breakthrough is when you go beyond being a manager. A leader has to spend their time on things no one else can do. If you’re doing something that others on your team could do just as well, you’re just wasting your time.”

This helps to re-enforce the above point. As a leader its important we’re doing and thinking about things our teams don’t have the the time to review.

The main goal when managing managers is to be their coach, sounding board, and unblocker so that they can achieve their own goals and those of their team. For the most part, this means having 1:1s that are more about coaching than solving, and framing your own role in the process with the right mindset.

This will help me re-frame my role with my team. This was a point of view I’ve had in the past – but lost more recently as the team has grown (and my purpose has drifted).

In cases where you aren’t an expert on the functional role, your value-add will not be knowledge specific to the role but rather your availability as a thinking partner on broader skills: strategy, communication, problem-solving, management, and so on.

This is especially true the more senior you get in an organisation, as you can’t be an expert on everything your team does and can do.

I expect you are making decisions a lot without me, and if you come to me, I’ll usually put it back on you with “What do you want to do?” or “What should you do?” and help you decide. That said, if there is a big decision brewing, I’d love to know about it, and I’m always here to talk it out. I like to know what’s going on with you and your team.

One of my team used to call this a “busby” question, and I think that stopped me using it. This has given me the confidence that I need to keep using this approach in future when developing my team and other employees.

Recruiting

Not using the rubric; asking different questions of different candidates, and therefore never finding a way to benchmark an excellent answer Not interviewing for the capabilities most needed in the role Assessing whether they like someone instead of whether the candidate will be successful in the role Overly prioritizing the right candidate experience rather than the right trajectory and aptitude to learn

These are common issues when recruiting. The key is consistency!

The best interviews suss out how someone: Works with other people Gets quality work done themselves Motivates and develops themselves Has or can develop the expertise needed for the role Demonstrates leadership and resilience

Its important to find someones passion when recruiting. Great quote here.

While you’re at it, watch for how much they use “I” or “we.” Too much “I” is a flag that they may not be humble or collaborative and you should probe further. Too much “we” may obscure what role they played in the situation, which is something you’ll want to clarify. I vastly prefer those who use more “we.”

This aligns with what I’ve been thinking for a long time. Anyone that is using “I” too much in their interview is not a team player and will likely act as a lone wolf.

Team Re-organisation

There are some who believe that reorganization or restructuring is always a sign of a problem. These changes can certainly be disruptive for employees, particularly those changing managers, but I would argue that needing to change the org structure can also be a sign of high growth or a strategic shift. If you’re lucky enough to be in a high-growth mode, it’s important to set expectations internally and normalize the fact that new organizational arrangements will be a common occurrence.

Team re-orgs are normal, especially in high growth organisations. They also give managers and new leaders a chance to take on more responsibility.

You can and should take time to consider whether a reorg is necessary and what it might look like. But be careful when you start involving others in the process, because the ice cream is now out of the freezer.

When you are doing re-orgs, move fast, and be careful who you involve in the process.

Team Meetings

I recommend including a “pass-downs” agenda item in your team meeting to share information from company leadership that’s relevant for your team members to know, either for context or because it directly impacts their work.

This concept of “pass down” agendas is something we are missing currently in this hybrid work mode. Overall we don’t document enough – which is something I’m going to look to change in 2024.

Snippets Executive team member name: Assigned action item updates—also in tracker General updates (e.g., whereabouts, travel plans, offsites) Potential topics for discussion and why they should be discussed Major company or product initiative status and learnings or customer contract negotiation status and learnings Top-level notes from a customer meeting or external event Launch, event, or PR plans in flight Info on top talent

Exec meeting agendas should include some common items that help to build momentum. Again – something I’m going to look to add to my meetings to support a more hybrid structure moving forward.