Are You Sabotaging Your Career? – Part 5

Your peers have been promoted and you haven’t. Your colleagues earn more money than you do. Your teammates get better, more interesting work than you do. What’s their secret?

They ask.

Talking to managers about your career can be daunting. They seem unapproachable. You’re uncomfortable talking about yourself or asking for things. You’re afraid of the answer you’ll get. Regardless of the reason, if you don’t ask, you probably won’t get the results you want.

When it comes to your career, we’ve covered the importance of perception, discussed three common career self-sabotage maneuvers, strategies to get noticed by executives, and how to escape the pigeonhole. This time, we’ll talk about the best ways to talk to your manager.

Lesson 5: Effective Communication with Management

Talking with your management is important. When I started working, I avoided my managers. If they were looking for me, I was probably in trouble. When I went looking for them, I would get myself into trouble. A mutual-avoidance strategy seemed ideal. Then the company offered my brother a position at a level below me. The hiring manager instructed, “Don’t talk to Stephen about the offer because it’s much more than he makes.” My brother simply left a copy of the offer letter (at 25% more salary than I was making) on my desk. At that moment, I realized that “hide and hope” wasn’t an effective strategy for dealing with management.

It also led to my favorite manager quote ever. When I brought up the pay inequity, my manager said, “You know Stephen, money won’t bring you happiness.” My response, “I agree, but the current lack of it is bringing me unhappiness. Let’s solve that problem.”

Tip 1: Bring Answers – Not Problems

Engineers complain that they cannot convince their managers to take action. How can they break out of their pigeonhole if all of their ideas are shot down? Many great engineers have become managers just to get the authority to drive their agenda – only to find out that they still have a boss who says “no”.

How can you turn your ideas into reality? First, come with more than a list of problems. Most times, I see people approach their managers with the template, “X is really broken. It’s going to be a disaster. We should do something.” They then look expectantly at their manager, waiting for guidance. Next time, try using this template, “X is broken. Here is the projected impact. The team thinks we should do ‘Y’ in the short term, and ‘Z’ in the long term.” Junior engineers come with problems, senior engineers come with answers, and technical leaders come with results (Note: engineers who try to hide the problems end up unemployed).

A tale of three engineers. Long ago I had built a replication product that could no longer scale to meet customer requirements because of my terrible thread-intensive design. Every week for a couple of months, the “lead” engineer spent 30 minutes rehashing the problem without suggesting an answer. Sabotage pt 5 pic 1After the second meeting, I spent those meetings trying to squeeze my wallet out of my back pocket by flexing my buttocks. About a month later, a staff engineer delivered a proposal (supported by the senior architects) in which a team of 2 people could solve the problem in 9 months. We adopted that proposal. Finally, two weeks later, over the Christmas shutdown, one frustrated new hire just re-wrote the code, including an automated test suite. The manager moaned about fitting the work onto the release train, but he was thrilled to solve our biggest problem a year early! Guess which engineer became the Lead Architect in three years, which engineer led the next project, and which engineer was sent to the bench.

Coming with code isn’t always the right answer, but coming with answers and results is more effective than coming with problems. As my boss says – “If you’re asking me to solve your problems, why do I need you?”

Come with answers to problems; even better, come with results.

Tip 2: Think about career path, not promotion

Too often, people focus on an individual promotion, rather than the arc of their career. The conversations with their manager become transactional (e.g. “I want ‘X’, or I’ll do ‘Y’”). This signals that you don’t want a long term relationship in which both sides invest in one another. Instead of collaboration, you end up with negotiation. Furthermore, it leaves the engineer with insufficient skills and opportunity to further grow their career.

First, promotion discussions are painful because they start too late. Judge these 2 opening lines:

  • Opener 1: “I enjoy my role, but I’d like to talk through the available career path options. What is the target destination, and what I do I need to do to take the next step in my career?”
  • Opener 2: “I’m really frustrated. Everybody else around me is getting promoted. I don’t see a future here, since you don’t value me.”

In the first case, you’re open and your manager will be delighted to help grow you (if not, that may be a sign that you’re way off track – which is also useful to know as soon as possible). In the second case, you’re angry and your manager will be defensive. Unfortunately, I hear far more of Opener 2 than Opener 1*. That’s why promotion discussions are so painful for people.

The main difference between the two openers is time. In the first case, you’re happy and planning for the future. Managers will want to collaborate with you. You can plan out a career path, developing skills, relationships, and credibility as you grow. You’ll be ready for the new roles and responsibilities of more senior positions, so you can continue to expand your carer.

In the second case, you’ve waited too long to take action and you’re threatening your manager, demanding instant gratification. Managers may give in to the threat, but you won’t have built up the skill set or support to succeed in the new position. Peers and junior staff will wonder why you’re at such a senior level. You’ll feel isolated and irrelevant despite your “senior” position. Because you are.

*Ironically, it’s the people most uncomfortable talking about themselves that end up with Opener 2 because they wait so long to discuss their career. To get over that concern, change Opener 1 to – “How can I help the company even more by taking on a bigger role?”

The secret to any promotion discussion is to start the conversation immediately. Sabotage pt 5 pic 2

Second, career paths and promotions get off track because you get become indispensible. Most companies promote you only after you’ve proven that you can succeed at the next level; they don’t promote you and hope you’ll grow into the role. Therefore, to make it to the next level in your career, you need to display a mastery of those new skills. You can’t do that if you’re spending all your time doing your existing job. Moreover, if there’s nobody to replace you in your existing role, you’ll still be stuck. Therefore, it’s critical that you engage in succession planning with your manager. This only happens if both sides believe that this is more than a transactional relationship.

Succession planning is an extraordinarily challenging work task. First, each of us worries that if we train our replacement, we’ll become expendable. Second, each of us (especially CEOs) secretly believes that we’re unique and indispensible; how could anybody adequately replace us? Third, it’s always more difficult to teach somebody to do your job than just to do everything yourself.

Succession planning is also an extraordinarily important work task. First, if you don’t have a replacement, you never get to do something new. Second, by working with somebody new, you can learn new approaches and methodologies that could help you in your next role. Finally, mentoring and growing others is part of becoming a leader.

Unless you want your existing job for life, work with your manager to include succession planning as part of your career growth. You must initiate the discussion because most managers are afraid of their employee’s reaction if they bring it up. You want to work yourself out of your current job, not become indispensible in it.

The secret to a successful promotion strategy is to work with your manager to find your replacement.

Sabotage pt 5 pic 3

Unfortunately, most people handle promotion discussions poorly. I had a newly transferred employee who made every mistake possible. Five minutes into my first meeting with him, he said, “Everybody that joined at the same time as I did have been promoted by their managers. I need to be promoted, too.” At that time, my kids were 3 and 5, so even his entitled tone of voice sounded familiar. When I tried to direct the conversation to how he wanted to grow his career, he said that he wasn’t motivated to work without a promotion. When I pointed out that I couldn’t promote him based on other people’s work in a completely separate group, he complained that I just didn’t understand engineering. Two weeks later, he repeated the same demand. He had not done any productive work. He also refused to let anybody else even look at his work – even encrypting all his files – so that he couldn’t free himself from his current job.  Two weeks later, he gave me the world’s funniest ultimatum – “If you don’t promote me, I’ll quit!” My response was simply, “OK. I’ll have HR walk you through the resignation process.” His ego would not let him backtrack. He ended up at another company at a lower job level.

The secret to promotions is to treat them milestones on your overall career path, not as the ultimate destination.


Individual contributors struggle to talk to their managers. Regardless of the reasons, communication with your manager is critical to turning your ideas into reality, moving your career forward, and getting the recognition you deserve. Hiding from the conversation only allows tension and trouble to build up. Approach your manager with solutions, not just problems. Collaborate with them on defining your career path and the necessary steps to make it happen. Most managers genuinely want to help their team; you need to help them help you.

If you think working with your manager is scary, in the next post, we’ll talk about how best to work with executives.

Engage your manager early, often, and collaboratively.

Stephen Manley @makitadremel

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