3L

The best advice for newly hired Technical Leaders

Looking back at the past 2 decades of my career, it looked like this:

• Every time I started a new position with a lot of passion, ambition, and my best ideas about how things should work, I failed.

• Every time I didn’t care as much and saw it as a temporary job, it went way past the expiration date, and I stayed longer.

Initially I didn’t have enough data points to see the pattern, but over time it was evident. I still didn’t know the reason until I got the advice I’m about to share. I wish I had known this earlier. It would have saved me so much pain and suffering, but that’s exactly why I’m sharing this with you.

The setup

When I started my Senior Staff Engineer position, I wasn’t sure what to expect. My new manager was a Senior Director with many years of experience at multiple well-known brands. He was also an avid reader unlike me.

Before I started, I sent him an email asking about his expectations for my first one hundred days. I didn’t hear back for a few days.

Then I got a 7 (!!!) page PDF!

Instead of telling me what to do, it laid out a mindset, a framework if you will, for how to approach this new position. The advice was too good to gather dust in my inbox, so here we go!

What?

Following is a copy/paste of the advice I got with some minor editing to remove company-specific information:

We strongly believe in starting any new job by applying these 3 L’s:

1. Look — what do you observe? Who does what? In meetings with the teams, when the manager is present, when they are not, etc. Do people look engaged, happy, sad, scared, etc.? Who’s the go-to person and most often seen in various meetings? Who’s taking up all the airtime in interactions, who’s silent? Why?

2. Listen — What are people saying in person, in meetings, on slack, in RFCs, etc.? Does what you hear match what you see? Does what’s said match what the team and managers think they do in terms of behavior and actions? If not, why? How is what’s said by leaders interpreted? And if there are misinterpretations, what consequences does it have on the org and product?

3. Learn — Try to avoid the “at my old job we did…” argument. Have an open mindset about learning what the new place is doing and how they do it. Go with the flow, even if you don’t agree with how things are done (within reason) so that you really understand their ways of working (WoW) with no judgement. This is a vital part of building rapport and showing that you are willing to be part of the group. Take note of what needs to change but the key is to understand the root cause instead of trying to change the symptom.

The ability to unlearn the old and relearn is the trickiest skill to master for senior professionals.

Why?

Coming in with a lot of experience, it is easy to assume a link between the new problems and older solutions. It is easy to overlook a company’s uniqueness and blindly throw the baggage at the new job. This leads to premature solutions that don’t fit.

This risk is even higher after a longer employment period for a senior position.

Broadly speaking, there are four categories of things that can be new at a given environment:

• Tech: the actual technical solution in place and its maturity in terms of DevOps, security, reliability and architecture

• People: the culture, org structure and the type of talent making up the company DNA

• Operation: the way of working (WoW), processes, facts, assumptions, and beliefs (or FAB as

  John Cutler
  puts it.

• Product: the context of the problem the business set out to solve and its business model and customers

Put together, I call it T-POP. The T is especially important for technical leadership positions like Staff Engineer, but the others aren’t less important.

Skipping 3L, there is no guarantee of relevance for any newcomer.

That was exactly my problem that led to short/long employment intervals.

The higher my position, the more pressure I felt to contribute as soon as possible. The more I cared about a job, the more frustrated I felt when I was not impactful.

How?

The advice I received went on to elaborate action points to make the 3L work:

Communicate: it’s good to communicate that you are in the 3L mode, and you would like to stay there for a while. This helps manage the expectations and reduce pressure on you to deliver from day 1. In my experience this [communication] lead to people respecting and trusting you more since you’re not that new leader who wants to change things because “you’ve always done it that way”.

Network: It will be your manager and onboarding buddy’s job to make sure you get access to the right forums and discussions on all levels, so you can make the right observations across the organisation. You must also spend a significant time during this phase networking and building relationships with key individuals in the org, individual contributors, managers, and stakeholders.

Analyse: form your understanding and communicate it back to make sure you understand. Develop hypotheses about how things could improve without directly mimicking your experience from another job. Do your homework to tailor your experience and ideas to the new environment. Everyone can complain but only those who have a solution deserve to act. Everyone can come up with an idea but only those who can drive action deserve credit.

Then it set some expectations:

It is only after this phase that you have the understanding, credibility and influence required to make changes.

This is a team effort where the leadership can support you but only if they feel like you know what you’re talking about. You’ll only have a few shots (most probably 1) so make sure to do your homework in advance.

This is also where you need to really show your follow-me leadership by showing how it’s done instead of ordering people or expecting them to read your mind. There are a lot of people with the self-assigned “leader” title who draw pretty diagrams, but only a few can turn those ideas into action and code.

When?

Originally, I got this advice for my first 100 days and here is a rough suggested agenda:

1. Spend the first month with the 3L.

2. Spend the next month formulating a hypothesis for where you can add value. Define good looks and how to measure success. Get feedback and verify your mental model. If possible, execute a small change to gather data and insight.

3. Scale up your initiative across the organization while measuring success and having all feedback channels open to adjust course. Don't rely only on metrics alone. Impactful insight is often hard to quantify. Metrics lag. Measurements are nuanced. Data may be missing. Get out of your comfort zone and talk to people and work by their side to gain first-hand insights. Use that insight to drive action.

Personally, I like to write a strategy documents for initiatives that span more than a few weeks because:

1. Writing helps me think better, especially when formulating a problem.

2. It is easier to get feedback at scale on a document than a meeting or presentation.

3. It serves as a track record for what was decided. That way the initiative can go on even if I leave the building.

4. It helps unify people at scale. Anyone who is involved with the strategy execution can refer to the document to self-align

Conclusion

My worst onboarding experiences happened when the expectations were high from the get-go!

Let’s face it: when someone is new, they don’t have the leverage to challenge those expectations. They want to show their best. They have probably set their own bar even higher!

Cut them some slack to let them look, listen and learn the tech, product, operation, and people aspects before developing a hypothesis about their impact.

PS. a connection recommended this book on the topic: The First 90 Days: Critical Success Strategies for New Leaders at All Levels.

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