An Elegant Puzzle – Part 5

This week we discussed sections 3.6 through 3.11.

Houston asked how often you get guarded time to pay down tech debt, as it depends on management buy-in. Jamie has used this tactic: “If you want Y, we have to fix X so it’s easier to add Z later.”
We thought it was interesting that it’s okay to hit a point where your system doesn’t scale: It means you didn’t over-design it. It was designed appropriately for the previous constraints.
You’ll always chase your tail on new technology. Weigh the pros and cons of LTS (long-term support) and the latest and greatest. There’s always maintenance work to do. Geoff said it’s depressing to never get caught up.
Don’t start with the easiest migrations. You learn lessons that will help you with the others. Jamie said it depends on your skill; if you’re not as experienced, you may fare better to start small and build up wins/trust.
Don’t do migrations partially, because you’ll lose trust. Houston’s suggestion: Define what “done” means in advance. Jamie’s suggestion: Define milestones and stages.
Don’t celebrate until it’s done and delivering value.
“Stop the bleeding” — like field medics. You have to triage, as some things may not be worth the time (e.g., working on a legacy system when you’re just going to replace it in the short-term).

The author suggested not to reorg to work around a bad person. What came to mind for Geoff was a person that ticks many “good” boxes but also ticks some “bad” boxes.
Jamie is experiencing a reorg at his company, which is dealing with the COVID-19 pandemic. The company has to figure out where their remaining staff need to focus; some projects may be temporarily unstaffed.
Re-orgs are rarely clean; there are more questions than answers.
We chatted about projecting head count in advance, as Geoff hasn’t seen much of this in his experience (i.e., hire to backfill or when a new contract is won). You need to optimize to what you’ll need later on. If you’re a product company vs. contracting company, your staffing approach will be different.
The idea of defining interfaces between teams reminded Jamie of his former geography professor. Depending on if he was addressed as Bruce, Dr. Ralston, Department Head Ralston, he engaged with you differently and wouldn’t mix context (e.g., switch from formal to informal).
Have a spreadsheet to show where people’s homes are. It’s easy to get missed. Jamie has seen this before where whole teams weren’t on the list, which spooks people. A skills survey (i.e., who has what skills) is another useful tool.
People don’t process change well in large groups. Some people may not feel comfortable speaking up, too. This is a balance of sharing too much that spooks people vs. being secretive about it.

We all liked the “degrees of alignment”: I’ll do it, preview (hands on at the start), review (hands on at the end), notes (follow along asynchronously). Jamie said this is somewhat like the Eisenhower box (e.g., important + urgent = I’ll do it).
It’s important in any management transition to decide where to engage vs. where to hang back.
“Combine your controls and the degree of alignment for each, and you’ve established the interface between you and the folks you support. This reduces the ambiguity of how you work together and allows everyone to focus.”

Houston liked the idea of writing up as many goals for 1-5 years out, picking a handful to focus on, then sharing that with your manager.
It turns out that none of us (Houston, Jamie, Geoff) have done deliberate career planning. Do good where you are rather than following checkboxes. For example, some people want to make widgets and go home at 5pm. We need those people, and we shouldn’t shame people by saying their behavior is career-limiting.
With most companies, there’s limited room at the top. Both Houston and Geoff have experience working for government agencies, where someone has to move out for you to move in.
Does your company allow you to explore growing your skillsets?
We all liked the idea of thinking of your manager as your partner instead of your master.
Don’t just follow the same plan as everyone else; go to where you’re disproportionately valuable because of who you are and what you want. It’s too easy to not get opportunities because you don’t look the part. Be intentional. You can build out skills in other ways (e.g., managing open-source software is similar to product management).

Answer the question you want to be asked. Houston said this sounds like a great strategy, but it’s a little disingenuous if you don’t answer the question. Jamie said you can try to reframe it: “I believe the question you’re asking is X.” Jokingly, Jamie said Houston should get better at grifting, as demonstrated in the TV series Leverage.
Stay positive, as negativity fuels the fire more than you’d like.
Speak in threes to keep things focused and concise.
Geoff mentioned a Pluralsight course on crisis communication that was informative.

“Confining yourself to one leadership style is just too hard.” Geoff shared that what he’s read is that you need to understand the different styles as you’ll need them in certain circumstances. For example, in times of crisis lead from the front, in times of peace lead from behind. Also people respond differently to various leadership styles.
Leading without authority will force you to learn techniques to build trust. Also leading leaders is a different skillset.
Model/document/share is something Geoff and Jamie have used to great success. (Iterate locally on a process, document how to adopt it, share the documentation more widely.)
Often if you document something, people don’t question it as it has a sense of formality. Telling people verbally is often not enough.
The author shared that model/document/share leads to more adoption than top-down mandates.

Geoff Mazeroff