You just landed a new and exciting role in a major corporation. The job description excites you the most: you'll drive strategic changes with a strong mandate. You'll play a key role in the company's journey towards becoming a more effective product and engineering organization.

Soon, though, the chords of Pink Floyd's Welcome to the Machine start playing in a loop in your head: you're faced with resistance, defensiveness, and the inherent inertia of a big organization that has always done things in a certain way.

You discover a massive rift between what your job description sounded like in theory and the reality on the ground. As you feel alone against an oversized machine with no leverage points, you start wondering if it hadn't been a big mistake to sign up.

Sounds familiar?

We discussed exactly this topic in one of our recent calls with the Sudo Make Me a CTO community¹, and what follows is a summary of suggested approaches and attitudes to adopt when facing similar situations.

You'll find it particularly helpful if you've spent most of your career in startup environments and only recently took on a role in a bigger organization. These aren't inherently better or worse than small and nimble companies, they're just different. What worked there is not necessarily going to yield good results in this new environment.

You decide whether this is a fight worth fighting

Before we get into the practical recommendations, it's key to have an honest discussion with yourself to decide whether you think it's worth putting in a lot of effort to change things, or whether it might just be more convenient to adapt and align. I don't see this as a moral dilemma as long as you're honest with yourself and the people around you.

As I often repeat, your career is only one of many contributors to a larger and arguably more important sphere: your life. Your job and career should help you build and sustain the life you want, though we often fall into the trap of taking this backwards. Therefore, depending on the stage you're in your life and your current priorities, it would be perfectly normal to decide to deal with the situation in opposite way, such as:

• Take it easy and go with the flow: you might realize that just taking it easy, adapting to the current standards, and following along will allow you to reduce work-related stress and dedicate more time and energy to other endeavours: learning new skills, your family, a side project, or even a hobby. Nothing bad about that as long as you're meeting expectations and don't lie to anyone.

• Deploy all your energy and skills to have a massive impact: this challenge might represent a great opportunity for you to learn rare and valuable skills that will help you pave the road towards your desired future lifestyle, whatever that might look like. In this case, you'll probably opt for an all-in approach where succeeding in overcoming the challenge of an organisation resisting change becomes your primary goal for a certain period. Nothing bad about that either, as long as you're clear with yourself and those around you that this will require certain sacrifices.

In between those two extremes, you have plenty of nuances to choose from. The specific shade of gray you end up selecting matters less than going through the exercise and being deliberate. Make sure you reflect and agree with yourself on the posture you want to adopt. Write it down: it will serve as a reminder on the days when you'll feel hopeless, tired, or fed up.

If you have decided to take the approach of taking it easy and taking advantage of the situation in different areas of your life, I bless you, and you probably can stop reading right here.

If instead you've decided on one of the many options in which you're determined to invest time and energy to change things, read along as we're now getting into the practical tips space.

🗺️ Step 1: Draw Maps of the New Environment

There is a great chapter in Tanya Reilly's book The Staff Engineer's Path², which is all about drawing maps of the various systems a Staff Engineer has to deal with, mainly platforms and organizations. That practice is beneficial for anyone with management or leadership responsibilities, especially when joining a new and largely unknown organization.

I recommend you start there, and the reason why it's deceivingly simple: before you can change anything, you need to know it, understand it, and be familiar with the rules of the game. How do you do that?

• Be an Anthropologist: Observe meetings, interactions, and communication styles among the people surrounding you. How are decisions made? Who holds the formal power? Who calls the shot? Who are the most influential people around?

• Be an Archaeologist: Which past decisions led to the current reality? Why were those decisions taken at that time? Who was involved? What are some of the approaches the company failed to adopt? Why? There is always a long list of decisions that led to the current state of affairs. Understanding them and their motivations is key.

• Map the Stakeholders: Who are the key players, potential allies, and those who might resist change? Identify their motivations and concerns. Particularly in the case of teams or individual who might see their role redefined as a consequence of the transformation you'd like to push.

• Understand the Context for the Transformation: If you've been hired specifically to contribute actively to an ongoing transformation, you want to know everything about it: where did the change initiative originate? Who are their champions? Who are the main sponsors? What are the stated goals? Are they different from the underlying objectives? Who reports to whom?

Do not underestimate the time it'll take you to map out the whole environment, and be at peace with it. Though it might look like nothing is happening during this phase, you're paving the way for all future actions. Rush this step, and you'll jeopardise your ability to have an impact later.

🎯 Step 2: Clarify Your Role

Do not assume that those who wrote your job description have total clarity on what they expect from you. Oftentimes, they just have a vague idea, and they hope you'll help make it clear through your observations and recommendations. Consider the original job description as a starting point, rather than the destination.

Some ways you can go about it include:

• Document the Gap: Acknowledge the difference between the ideal role you've been offered and the current reality. Document it, and use that work as support for discussion with your manager and your key sponsors. Make sure you're creating shared understanding about the gap, so that people can support you in bridging it.

• Propose, Don't Assume: Develop your own job description or pitch deck to communicate its key aspects and rationale. Focus on the value the role will bring to the company and clarify the desired responsibilities as well as how you'll be interfacing with others in the org. You can use tools such as a RACI matrix to formalize and communicate the role's responsibilities and interdependencies with others.

• Start with Your Sphere of Control: It's important to prove your worth and capabilities in areas you already have full control of. Build credibility there as you work on your ideal job description. Resist the temptation to start from concerns currently outside of your control. Get your act together first, and use that reputation to expand your influence.

• Suggest Incremental Expansions: Once you've proven your worth on the daily job, seek buy-in for small and incremental pilots to gradually expand your role into new areas. Start with low-risk ones, but make sure you can prove and document the value of the change. Then gradually turn up the knob.

During this phase, it is crucial to balance patience with seeking quick wins. Make sure you document all the changes and improvements you're able to make. They'll come in handy both as a way to motivate yourself when you feel impatient and to prove your impact with the larger organization.

🤝 Step 3: Build Bridges, not Walls

You won't succeed in driving changes if you're facing a horde of enemies that see you as a threat. You need the support of a large group of people to make those changes successful. You win them over one by one by building rapport and establishing trust. Here is how you can do it:

• Focus on 1-on-1 conversations: Don't limit your interactions to group meetings, and proactively schedule both ad-hoc and recurring individual conversations, especially with the key decision-makers and those who seem to be the most defensive. This will allow for more candid discussions and will give you a lot more context around their postures.

• Listen first, then talk: Don't turn those meetings into selling calls. Show a genuine interest in understanding the other person's point of view, what motivates them, and their incentives. Ask plenty of questions, and resist the urge to argue immediately when you disagree. Empathy will disarm defensiveness, which in turn will open the space for your ideas and suggestions to be received more constructively.

• Find Allies: Connect with peers who are also navigating similar challenges and are moved by the same or aligned goals. Share insights and perspectives with them. Agree on collaborative actions and build a compact front that will have a bigger impact than isolated individuals.

• Focus on the Company's Agenda: Frame all your initiatives and proposals in the context of the company's interest and benefit. Emphasize how your proposed changes and ideas can help achieve everyone's goals, not just the ones attached to your role. Make it as impersonal as possible.

People rarely resist change out of malice or a hidden agenda. Most often, that resistance is driven by fear, concerns, or misunderstanding. As you get to know people more and show a genuine interest in them, they'll increasingly trust you. Make sure not to betray that trust, and always operate with the company's interests in mind.

♻️ Step 4: Drive Change, One Piece at a Time

As you've created the conditions for change to finally happen, you need to ensure you have solid plans, strong execution, and an exemplary ability to adapt as you collect feedback and observations. During this phase, a few techniques will prove beneficial:

• Strategically Document Everything: A decision does not exist unless it's written down. Accurately capture meeting notes and circulate follow-up summaries with all participants and key stakeholders. Seek explicit confirmation and virtual stamps of approval where appropriate. This paper trail will help you create clarity and accountability. It'll also provide a role model for the entire organization.

• Set the Pace of Execution: Propose regular follow-ups, even if they're received with resistance initially. Do show respect for other people's calendars, but don't fall into inertia. Frequent short meetings are better than longer but less frequent ones. Set clear agendas, establish explicit deadlines for actions and deliverables, and follow up on them.

• Pick your battles: As you make progress, you'll see plenty of opportunities for changes and improvement. Duly document them, but resist the urge to open too many fronts. Focus your energy on those changes that will have the most impact and are most achievable, and be at peace with the rest.

• Iterate and Adapt: While your determination to achieve the goal is key, being stubborn about how exactly you get there will generally backfire. Plus, that wouldn't fly well with people you're effectively asking to change and adapt. Make sure to regularly assess your approach, collect feedback, and course correct when needed.

This stage is when things happen, but not every action will lead to the expected outcome. Focus on executing well, on driving accountability, and adapting to new insights to maximise the positive impact over time.

🥵 Surviving All This

Along this long journey, you'll encounter plenty of opportunities to lose your sanity and motivation. There will be plenty of ups and downs, and the occasional I'm out of here days. Some tactics will help you stay sane and healthy as you go through this.

• Cultivate Patience: One of the biggest challenges people face when they go from being a Software Engineer to taking on a leadership role is the nerve-wracking expansion of feedback loops. In your previous role, you got used to getting almost instant feedback on the outcome of your decisions. Now it can take days, weeks, or even months. This is even more the case in large organizations. Patience is an undervalued yet extremely powerful skill in this industry.

• Don't go against the Company's Rhythm: In a crash between a cargo boat and a powerboat, the cargo boat wins. Instead of being the powerboat, learn to nudge the cargo boat in the right direction.

• View it as a Learning Experience: Navigating these challenges is a huge opportunity to acquire rare and valuable skills, especially for those who aspire to more senior engineering leadership roles. Think of it as someone paying you a salary to do the equivalent of an MBA.

• Celebrate Wins: No matter how big or small they are, take the time to appreciate the improvement and incremental progress. This will help keep you motivated and sustain momentum.

• Embrace Seasonality: You can't always push with the same intensity. There will be periods in which nothing seems to happen, and moments in which everything falls into place. Embrace the natural seasonality of human activity, and learn to appreciate it.

The most important part is to remind yourself about why you're doing it. Regularly reassess your motivation, as we discussed at the opening of the article.

Be prepared to discover that your motivation has changed, at which point you should adjust your approach, too.

Always be deliberate at any moment, but accept that the stated direction can change over time.

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Highly recommended book not only for Staff Engineers, but also for people managing them. You can find it here. I wrote my review of it about a year ago, in case you want to read it before you buy

📚 Books I read in May 2024 Sergio Visinoni · June 12, 2024 Read full story