Hello friends.

This month, I want to focus on an area of professional growth I've seen some people struggle with recently, and I'd like to see you avoid that struggle. As you navigate your professional journey, you'll encounter the challenge of adapting your tried-and-true "playbook" to new situations. This can go horribly wrong if you don't consider the factors that made your playbook successful. In this issue, you'll see the pitfalls you can run into and how you can adapt.

But first, I'll share a tool I've been using to track my time on projects right from my Terminal window that I think you might find helpful if you're in an environment where you need to be accountable for your time at a more granular level.

Tracking Time with TimeWarrior

I've been juggling a lot of tasks lately. In addition to my responsibilities as a functional leader, I've been working on some technical tasks because I haven't been able to delegate them yet. I haven't tracked my time on individual tasks since I was a freelancer, but I recently decided I needed to do a better job of accounting for my time.

I've been working with a small CLI tool called Timewarrior that lets me record the time I spend on things right from my Terminal window.

Installing it is as easy as using your package manager. If you're on a Mac, you can install Timewarrior with brew:

brew install timewarrior

Once installed, you can run the timew command once to set up the default configuration and database file.

Then you can start tracking time. For example, to track the time you spent writing a newsletter, you'd use the following command:

timew start "Newsletter"

This starts a new timer and tags the entry with the name of the task you're working on.

Timewarrior shows some output on the screen as a result of the command:

Tracking Newsletter
  Started 2023-09-29T00:51:03
  Current                  03
  Total               0:00:00

Once you've completed the task, or you need to switch gears to some other project, you use the timew stop command, which stops the timer and shows some results:

Recorded Newsletter
  Started 2023-09-29T00:51:03
  Ended                 53:44
  Total               0:02:41

To get a summary, use timew summary:

Wk  Date       Day Tags         Start     End    Time   Total
W39 2023-09-29 Fri Newsletter 0:51:03 0:53:44 0:02:41 0:02:41

                                                      0:02:41

The summary shows the week number, the date and day, the tag used for the entry so you can identify what you did, the start time, end time, and total time spent.

If you forget to record something, you can add an entry by specifying the start and end dates:

timew track from 2023-09-28T17:00 to 2023-09-28T18:00 "Newsletter"

The timew summary command only shows the current day. Use timew summary :week to see the whole week's time report:

Wk  Date       Day Tags          Start      End    Time   Total
W39 2023-09-28 Thu Newsletter 17:00:00 18:00:00 1:00:00 1:00:00
W39 2023-09-29 Fri Newsletter  0:51:03  0:53:44 0:02:41 0:02:41

                                                        1:02:41

The documentation is detailed and covers more advanced usage.

Timewarrior is helping me track where I spend my time each day. It's working well for me because it's not a heavyweight tool that makes me jump through a lot of hoops to enter the time. You should give it a try and see if it works for you.

Your Playbook is Not Universal

If you've had some success doing your job a certain way, you've developed a working mental model of how to work and how to solve specific problems. This model is your personal "playbook" you use. It's your strategy and collection of tactics.

Eventually, you leave your job, move on to a new one, and, of course, you bring your playbook to your new company. This doesn't always go well for people. A playbook is only one piece of the puzzle, and you might not be aware of all the other things that contributed to your success.

New and less-experienced leaders are especially likely to fall victim to this trap, but individual contributors get caught here, too.

The first thing people forget when they try to run their playbook in a new situation is that the people who made it work aren't there. The people you work with have a significant impact on successful outcomes. Those plays you ran worked because of who you worked with and the skills those people had.

When you join a new company, you'll have different teammates with their own established practices and playbooks they're using. You won't have your old team with you, and you'll fall out of favor with your new team pretty quickly if you keep referencing how you used to do things at your previous job. More importantly, some things in your playbook only work if you have the people with the skills and knowledge to pull them off.

This is why you tend to see senior leaders bringing in their own people after they join a company. They have a playbook and know they need the right players to execute those plays. Unfortunately, this creates tension in the new organization, especially if people get laid off to make room for these new players.

And the playbook still might not work because people are only one factor in making a playbook work. The new company may have different constraints or different goals that make it much harder for you to apply your plays.

It's common for people who moved from a massive company to a role at a small, scrappy startup to struggle to execute their plays. In a big company, the roles and processes are often well-defined. The playbook you used in your last role is based on those particular situations and procedures. Sometimes, someone else established those processes and procedures years ago, and you happened to inherit them.

The small startup will expect you to build out the things you took for granted at BigCo, and you might not be equipped for that. For example, if your playbook relies on tracking users through the funnel, but your new organization hasn't set up any of the funnel metrics yet, you must figure out how to make that happen first.

It's easy to confuse the tailwinds created by the contributions of others and the existing established processes with your own success. This only becomes apparent when you find yourself without those people and processes. And it becomes clear quickly to everyone who works with you as you struggle to have an impact in your new role.

Finally, the business may have different goals for your function. You may be serving a different audience or building a product for a market wildly different from what you know. For example, imagine you previously worked at a company responsible for creating tooling for general audiences, but you now find yourself focusing on tooling for developers at Fortune 100 companies. There's a good chance your playbook won't be very useful without many changes.

So how do you move forward? You obviously can't throw out your whole playbook. But you can take some steps to adapt.

First, listen and observe when you join a new company. Keep your opinions and thoughts to yourself for the first few months unless asked. Of course, you were hired because of your experience, but it's good to take some time to figure out how things and people work when joining a new company. Be humble. You don't have all the answers because you don't know what you don't know yet.

Remember Chesterton's Fence from Issue 7? Apply that lesson here; don't tear things down until you understand why those things exist first.

Second, ask others to share their playbooks with you. What are the tactics they find successful in moving things forward? Who are the key players that make those things work? Get their advice. They may have built the processes and procedures you'll work within. Seek to understand them.

As you learn more about the organization, you can start looking at how you approach work, see what parts of your playbook still apply, and what pieces need tweaking.

The more experience you have and the more inputs you take, the more robust your playbook will be. You'll start thinking about things more holistically and be able to adapt more quickly to each new situation.

The worst thing you can do is come in and try to force your playbook on your new company. You'll struggle to have a meaningful impact and may alienate the people who could help you succeed.

Parting Thoughts

Consider these questions as you reflect on this month's issue:

1. Have you experienced a peer or leader attempting to use their unmodified playbook in a new environment? What was the outcome? What factors contributed to the outcome?
2. Consider the roles you've had in your career and the industries you've worked in. When you changed jobs, what were the things that stayed the same, and what were the things that were significantly different? How did you adapt?

As always, thanks for reading. See you next month!