What Great Leaders Look Like according to Bill Campbell

Trillion Dollar Coach is a great read (or listen if you’re an audiobook fan like me) about Bill Campbell, a football coach who pivoted mid-career into a business executive in Silicon Valley, as an executive at Apple, a CEO of Intuit, and an executive coach to Steve Jobs and other high profile leaders.  The book talks about some the qualities he looked for in leaders, which I found very useful to consider as I think about how what I look for when I’m interviewing or considering someone for creased responsibility:

  • Smarts:  Ability to learn quickly and apply new concepts in novel ways
  • Hearts:  Ability to empathize with and understand others
  • Grit:  Ability and willingness to work hard
  • Curiosity:  Desire and openness to continually learn (Avoid people who “have it all figured out” — instead you want people who always have more questions)
  • Winning Right:  A desire to win the right way, with a team-first attitude and integrity, all the time not just when it’s easy
  • Humility:  Pay attention when people celebrate other teams or leaders succeeding, not just themselves
  • Sacrifice:  Pay attention when people are willing to sacrifice something for the organization, another team, or a customer


Effective Leaders see the Bigger Picture

It’s easy for leaders, especially ones early in their careers as leaders, to struggle to see the bigger picture (instead being focused on managing/coordinating/triaging the day-to-day operations of a team/department/division (losing the forest for the trees).

When that happens, inexperienced leaders may respond to big capacity/schedule/velocity issues by just trying harder without stepping back to evaluate if their targets are attainable based on current resources and approach.

I’ve seen leaders drive their team harder and harder, working nights and weekends without realizing that even with that surge in effort, they’ll still miss the deadline/target by a huge margin without going to senior leaders and asking for help.

When you realize you’re in over your head, go to your senior leaders, mentors, or peers ASAP — it’s only going to get worse.  Maybe you need additional people (even if that hurts profitability in order to meet a commitment) or maybe it’s a technology investment to allow efficiency gains through automation.  Or maybe you need to consider changing the target/finish line.  Or something else.  But don’t assume you’ll figure it out later.

It’s important as a leader to make time (especially when it doesn’t feel like you have any time for planning/reflection/zooming out) to step out of the tactical view and assess how you’re doing against the bigger picture goals/priorities/milestones (see Drucker’s What Makes an Effective Executive).

And when the issue isn’t the team’s overall velocity, but your personal, individual busy-ness, it’s critical to realize that unless this is some unique, temporary burst of work, things likely won’t get any better by you just trying harder — you probably need to invest the time you feel you don’t have, to ask for more help, or better publish/share the knowledge about the work/procedures you do, or invest in training the people you have.

Don’t think you can dig out of a hole of crazy-chaotic-busy-ness, by doing the same thing you’ve been doing only faster — it probably won’t work (and you’re only making it harder for yourself to dig out later)

A Tip on those Hard Conversations

If you’re a leader, being able to effectively lead the tough, important, critical, crucial, game-changing conversations is a huge piece of being able to succeed.  It’s certainly worth reading great resources in this area like Patterson’s Crucial Conversations.

When you need to have a tough conversation with someone based on poor performance, you should first reflect on what you’re trying to accomplish and if you think that person can succeed in your organization (either in the current role or another role) — your discussion should reflect if you’re trying to coach someone who can succeed, or if you need to have a tough conversation with someone who needs to either be in another role, or who should consider another organization.  Think about which of these categories might best describe them (and be careful not to only use qualitative feelings to assess this — make sure you’ve clearly communicated goals and expectations and then measured them against those):

  1. Moderate/high-potential performer who needs coaching/mentoring to succeed in this role
  2. Moderate/high-potential performer who could succeed in other roles in this organization, but isn’t a good fit for the role he or she is currently in
  3. Someone you’re not sure about their interest/capability/aptitude to success within this role or other roles in the organization, and you need to quickly find ways to assess that
  4. Someone who isn’t a good fit for your organization and you probably need to have that tough conversation on if them moving on if the right move for you and them

When someone is on the wrong role, or in the wrong organization, it’s an exhausting and horrible experience for them, you as their leader, and everyone around them.9 box chart

A more nuanced way to think about this is to assess your people in the classic 9 Box Model to see if they need help moving up their performance axis, based on the potential; or if they’re in the wrong position, team, or organization.  The idea is that people get measured on the x-axis of current performance and the y-axis of potential (see below).


Replace recurring chaos with a RAM

Most teams have a lot of recurring tasks they have to keep track of, such as an HR team doing annual benefits ‘open enrollment’, or an IT Service Desk team reviewing weekly automated backup status messages, or an Accounting team doing their monthly book close, or that annual data audit people always forget to do.

Many teams remember those types of tasks in the heads of different people on the team. Some have recurring Outlook/G Suite calendar reminders.  Some have sticky notes.  Or smartphone alarms.  But all those approaches are prone to lots of issues (e.g. someone is sick on a key day, or someone leaves the organization and doesn’t transfer that knowledge well to new team members).

I’ve seen a lot of value in creating a centralized Recurring Activity Matrix (RAM), which can be a simple table in a wiki tool (e.g. Microsoft SharePoint, Atlassian Confluence) where a team can see what recurring activities exist, their frequency, and what procedure/checklist goes with that task.

I’ve found a great, simple, cheap approach is to publish that table and then create an automated, email reminder for each row using SendRecurring, which is a free or cheap service (depending on how many tasks you juggle) to send emails as a reminder, ideally to a system to ingest and publish them to the group, such as Atlassian Jira Service Desk (JSD).

Just creating this simple knowledge management tool and incrementally refining it, each time you identify something the group should know about it, is a great way to improve the operational resilience of a group, and drive people to identify the work they do (and ideally create procedures/checklists/processes to define them).

A RAM table could have columns like this:

  • Owning Team (if your organization has more than 1 team in it)
  • Task Name
  • Associated Task Procedure/Checklist (e.g. maybe a link to a wiki-based checklist or a formal process asset that defines the procedure)
  • Frequency (e.g. Weekly)
  • Trigger Day/Time (e.g. 28th of each month at 11am EST)

(I’ve written about this before, but I think it warrants another post because it can be so valuable for teams to do)

Maturity-based Management

It sounds obvious, but as a leader, it’s critical to manage a team based on the team’s current maturity level.  For example, if you have a high-maturity, high-performing team stacked with A+ players who know how to do their roles well, are excellent at the needed hard skills, and collaborate as a team incredibly well; you should not treat them like 5 year olds playing soccer. Conversely, you should not treat 5 year olds playing soccer like a high performing team (e.g. explained nuanced optimization concepts, when they’re still struggling with the fundamentals).

This sounds obvious, but often people try to focus on team performance metrics, such as Scrum team velocity or first-call resolution, when they should realize the team needs a lot of work on the fundamentals (e.g. ensuring the team understands their purpose and context within the organization, understanding why various meetings are held, clarifying expectations of speed vs. quality).

Top Priority for a Leader

It’s easy to undervalue leadership, and think that just being good at the “hard skills” of your career and telling your direct reports specifically what you want them to do will be sufficient, but as team’s and organizations grow, that doesn’t scale.

It’s also easy to think the most important priority for a leader is to build big, complex schedules with row after row of Microsoft Project tasks and a huge Gantt chart.  Or to conduct frequent sync-ups to drive work through your team.

But the most important thing a leader actually does is define his or her team’s/organization’s culture.  Great leaders create a culture that attracts and retains great people that align with that culture.

Sometimes that culture is focused on being a safe space where people can take big risks and it’s okay to fail (see Google’s Project Aristotle, see Google X). Sometimes it’s a culture that focuses on a purpose that people rally behind (an exciting mission by manned space flight or a noble mission like helping Veterans find post-military careers).  But whatever it is, it’s critical as a leader to realize that setting and maintaining culture (and actually making hiring, promotion, attention, firing decisions based on it) that is the most important thing a leader does.

Leadership 1-on-1 Tips from Bill Campbell

I’m enjoying the audiobook Trillion Dollar Coach about Bill Campbell, a football coach who pivoted mid-career into a business executive in Silicon Valley, as an executive at Apple, a CEO of Intuit, and an executive coach to Steve Jobs and other high profile leaders.  One of the great concepts early in the book is how to structure time on 1-on-1 with a direct report.  Some of the concepts including:

  • Discuss job performance, ensuring that you can clearly articulate what success looks like (not just qualitative discussions about how you’re feeling)
  • Discuss rapport with peers (while it’s important to monitor relationship/rapport/political capital with more senior leaders, the rapport with peers is critical to advancing initiatives (getting things done))
  • Is this person (your direct report) coaching, guiding, inspiring, and holding account his or her people?
  • Is this person continuously focused on identifying new ways to improve and mature?


Know when Working Harder isn’t going to Work

A dedicated employee who will work harder, with a greater sense of urgency (and maybe some extra hours when needed) is great.  But what’s much more valuable than someone with that work ethic, is someone who can see when working harder isn’t going to work, and they need to change their approach.

Think about someone using a dull saw to cut a huge pile of wood to build a house — they’ll look at the schedule and say “I don’t have time to sharpen my saw”, which is ridiculous to think about.  But we do it all the time when we try to shift into a higher gear and work harder to “dig out” of a busy season/project instead of thinking about what should we change.

It is so valuable as a leader to determine when a situation can be surged over, and when you need different resources/capacity/people/tools to overcome the situation.  Years ago, I was helping a Project Manager whose team was continually well below the needed velocity to get to the project’s finish line on time.  He kept trying to work nights and weekends to get back on the track, but simple math made it very clear that he could not single-handedly get the project back on track.  So we had to investing in both a technology and some additional people to help his team finish — it was easy to easy for those investments on his project; but it was much better to ask for them early in the project’s life as opposed at the end when he would be doomed to fail.

Think about if you need better processes/checklists, or a tool (e.g. software application) to help you be more efficient), or more people on your team, or something else.  Take the time to step back and think about how to change the game you’re playing so you can actually win.

Don’t Sleep in your Contacts… and the Importance of Communicating Risk Well

I went to the eye doctor recently, after my eye was bothering me.  I had slept in my contact lenses for several nights (which I’m prone to do), and my eye started bothering me.  In the past, when this happens, I take my contact lenses out, throw them out, and take a few days off of contacts.  This time however, my eye was bothering me much more than usual, so I went in to see the eye doctor.  I’m glad I did — I had a corneal ulcer, where bacteria had been stuck inside my contact lens. The eye doctor got me a prescription for some antibiotic eye drops and explained how lucky I was, since the ulcer wasn’t on the pupil itself (which can cause people to lose partial sight the rest of their lives!!!)!

The doctor asked me “Do you know you’re not supposed to wear your contacts overnight?” and I explained that I certainly did, but I had no idea what the real risks were — I assumed eye doctors said that, but that my approach to taking a break when my eyes bothered me was fine.

This is a great reminder of how important it is to communicate risks in a tangible, clear way.  It’s easy to say “That’s risky” or “This is not a best practice” or “It’s better not to do that”; but if we don’t take the time to truly articulate the possible impacts, explaining both the likelihood of something happening and the impact (severity) if it does happen, very bad things can happen.

Edward Tufte’s book Visual Explanations provides a powerful case study of this concept:  Engineers recommended the Space Shuttle Challenger not be launched based on specific weather conditions, but the launch was approved due to a lack of clearly communicating risk.

Are you Running in the Right Direction?

Early in my career, I was a leadership development conference (through Lockheed’s great Engineering Leadership Development Program), where we played a game called Gold of the Desert Kings  — it was a group game, in a big event space ballroom packed with engineers from all over the country.  I don’t remember the rules of the game, but I do remember that it was a powerful reminder of how important it is to plan before you start working.


It’s easy to say we should plan before we start doing work — people say things like that all the time:

  • Look before you leap
  • Measure twice, cut once
  • Cal Newport made this point on Ramit Sethi’s blog a while back
  • Agile Scrum “forces” people, every few weeks, to stop and assess where they’ve been (sprint demo), where they’re going (sprint planning), and how they could improve (sprint retrospective)

But while we talk about this often, most people often regress back to a tendency of “jumping in” under pressure, instead of taking a breath and investing the energy of actually building a plan.

At the individual level, people are very quick to start working, trying to “make progress” and “feel productive” without investing the time to validate that they’re working on the most valuable thing. When groups of people (teams) are involved, we’re even worse at this — not only does the team want to jump in to avoid the plan of group planning and not feeling productive, everyone wants everyone else on the team to be productive (busy) so they feel they’re not the only one working hard.  This creates this nasty culture where the team is trying to keep everyone busy (Instead, Goldratt’s The Goal teaches that we need to optimize the entire system, not at the individual person or machine level).

Yes the plan will change, but it’s not the first version of the plan is not the valuable part — it’s the exercise of pulling together all the different pieces of a project and thinking about them together that is valuable.

While making progress on some new task feels more rewarding and productive than building a plan, whether it’s an Agile backlog; a resource-leveled Microsoft Project file; and/or a few quick PowerPoint slides summarizing major activities, schedule, resources, and budget; INVEST the time to make a plan — make sure before you start sprinting in some direction that you’ve actually checked to see if that’s where you should be running.