Are You Sabotaging Your Career? – Part 6

Sometimes you see a colleague working with an executive, and you wonder how they got that opportunity. Then you see that same colleague isolated from teammates and managers, and you wonder if executive interaction is a good idea.

Collaborating with an executive can be a huge asset to your career, but it can also be a huge liability. Executives can expose you to unique roles and views of the business. Just as importantly, it gives the executive exposure to you. Unfortunately, through the years, I’ve seen many promising careers derailed by mishandling executive interaction – either by losing the support of the executive or alienating your team.

Since we’ve talked about escaping a pigeonhole and strategies to get noticed by executives, it’s important to also know how to properly engage and work with them.

Lesson 6: Effective Communication with Management

Caveat: I’ve found these tips to be useful in my career when connecting with executives. It also reflects how I like people to work with me. But, as with any person in the work environment, some executives are not worth your time. Some think they’re better than you and will treat you badly. Some will steal your work and take all the credit. Some will use you to advance their career and then leave you behind. So, be careful and pick somebody you trust.

Tip 1: Connecting with Executives – Personal

The best way to approach an executive is to simply reach out. One of my litmus tests for “high-potential employees” is whether they connect with me. Talk to me in the break room, use email or social media, meet through a mutual connection, or just set up a meeting. (Conversely, Joe Tucci seemed anxious when I introduced myself at the urinals. Similarly, NetApp President Tom Mendoza looked trapped when, as a new college hire, I burst into his office with my dad; fortunately, like Tom, my dad was a Notre Dame grad, so that smoothed things over).

During the initial encounter, be positive and concrete. First and most important, discuss what you’re passionate about, not what you think the executive cares about. You’ll put your best foot forward and you’ll teach the executive something new. I’m always thrilled to meet people who educate me – from User Experience to data analytics to sales processes to new coding methodologies. You can’t fake enthusiasm and knowledge, so bring your passion. Second, remember Tip 1 from working with your manager – bring answers, not just problems. More important, don’t complain about your management or peers; it makes a bad first impression and you don’t know if they’re already friendly with the people you’re critiquing (Note: For any serious issue with your manager or co-worker, go directly to HR.) Third, before you go in, have an idea what you’d like to see happen after the meeting. Getting to know one another is good; engaging on a meaningful project is better. Finally, if there is no natural connection, don’t force it. Executive turnover means there will always be other opportunities. As an engineer, I always reminded myself “I was here before you, I’ll be here after you.” (OK, I did actually say it to one VP – but I was confident that he was incapable of filling out the online forms needed to fire me).

A few years ago, an automation engineer asked me to support her plan for a new test harness. She was nervous because she assumed I was an expert on everything. After I asked remedial questions for 15 minutes, she realized that she was the expert in the room. After an hour, she had convinced me to support her test automation initiative. Within a month, her passion convinced me to change my job to lead QA and automation. Not surprisingly, she was one of my go-to people. It all began with her setting up a meeting and bringing her passion.

Tip 2 – Connecting with Executives – Public Forum

Connecting with executives in public forums (e.g. all-hands, town halls, public email lists) can be tricky. Done right, you can stand out as a leader and win the respect of both peers and executives. Done wrong, you can actually hear your colleagues whisper “career limiting move” as you ask the question. More often than not, I’ve been that latter engineer. At the time, I convinced myself that I was “speaking truth to power”; in reality, I was giving in to my need to be right. There is a fine line between asking challenging, important questions and being obnoxious. Actually, the line isn’t that fine.

The root question to ask – do I respect this executive?

If you think the executive is clueless, heartless, and/or worthless, then you’ll get no meaningful progress by publicly flogging them. Why waste your energy and expose yourself to retaliation? Sure, it’s fun to humiliate a buffoon in public. Unfortunately, the executives that aren’t respected tend to be insecure, petty, and vindictive. There is no upside, and significant downside, to attacking a worthless executive. How do you control yourself? Technology has saved me. I attend most all-hands remotely, even when I’m in the office. The technological divide keeps me calmer and less likely to say something I’ll regret.

If you do respect the executive, think about what they’re trying to do and what you want to achieve. Do you believe they’re aware of the challenges, but are oversimplifying the solutions? Remember that “leaders” are taught to project optimism (though not mindlessly, hopefully), to lead the team through the storm. If they’re not optimistic, how can the team be? Taking that into account, if you still think they’re missing something, bring the issues to their attention with the respect that you have for them. If you’re still not satisfied and you’re passionate about helping drive a solution, that’s a great opportunity to personally connect with the executive.

I worked with a senior engineer who wanted to take the next step in his career. He was told that hisSabotaage pt 6 pic 1 biggest limitation was an unwillingness to challenge and influence senior people like our CTO. He’d always just “agree and subvert”– not say anything in public, then grumble incessantly afterward. Therefore, he spent our next big architecture strategy meeting disagreeing with everything the CTO said. Finally, the CTO turned to him and announced, “There’s a difference between standing up for your ideas and being a passive-aggressive pain-in-the-ass.” He never did get that promotion.

Tip 3: Sustaining the Connection

Once you’ve connected with an executive, how can you turn that into a productive relationship?

First, you need to figure out if they’re actually interested in working with you. People will often express an interest in your proposal, but not follow through. Sometimes, they just don’t know how to turn you down. Other times, they don’t understand but are too embarrassed to ask questions; they’re just waiting for you to leave. Still other times, they are interested at the time, but it’s just not important enough to them to follow through.Sabotaage pt 6 pic 2

There is one simple measure for whether somebody is truly interested in your idea – time. If they’re willing to spend their time and energy on it, they care. If it never quite gets to their priority queue, then you don’t have a connection.

Second, you need to be persistent. I’ve had engineers abandon an idea because I didn’t respond to their first email. We all get so many emails; it’s easy to miss one. Now, if I don’t respond to 3 or 4 contacts, then the idea has failed the “time” test above. Don’t give up after one attempt, and don’t always connect in the same way (i.e. maybe email is a poor way to connect with a given person on a given idea).

Third, give them something they can do for you. Research shows that people like you better when they can help you. After all, we all like feeling useful. Therefore, don’t simply tell executives what you can do for them; give them something they can do for you. Make it something challenging enough that they can’t just send an email and be done, but not so challenging that it has to become a significant job for them. They’ll get invested in both the project and you.

In short, working with an executive is just like working with anybody else – from a 4 year-old to an engineer on your team (probably closer to the 4 year-old given the attention span). Connect, evaluate, stay persistent, and collaborate.


Tip 4: Your Team Comes First

The biggest risk in executive interaction is in alienating your manager and peers. They worry that you’re sharing information that makes them look bad, either with malice or unintentionally. They fear that your connection makes you harder to manage. They wonder if ideas won’t be fairly evaluated because you have executive support. Some will just be jealous.

Your team comes first because executives leave. They may leave the role, the company, or you. If you align to an executive over your own team, you’re likely to wind up exposed and alone.

I met an engineer who was introduced herself as a member of “Special Group X”. I’d never heard of it, so she explained that it had disbanded years ago when the executive sponsor had left the team for a promotion at a competitor. The team had been disbanded, but this engineer (and others) had isolated herself from her peers because she was “special”. Her career momentum stalled because she aligned herself with an executive that used her to vault up the corporate ladder. Her career stagnated because she never accepted it and she refused to rejoin her real team.

How can you avoid these pitfalls?

  • Advocate for your team. Sell them harder than yourself when you’re with the executive. If they suddenly get kudos for their work, they’ll know where it originated.
  • Share the information that you learn. In most companies, information is the modern currency. You now have access to more of it. If you share what you’ve learned with everybody, they’ll view you as an access point to information, rather than as a threat.
  • Stand on your own. Never, never, never use, “Exec X said” as an argument. Either your ideas stand on their own, or they’re not good enough. Use the information and perspective you’ve gained to bolster your position, but never “because he or she said so.” It enrages both your team and the executive you’re quoting.
  • Execute. Even if you start working on a special project, don’t let your existing work suffer.Sabotaage pt 6 pic 3

If you want to become a leader, you need a team to follow you. Executive support is valuable, but history is littered with great leaders’ successors failing (e.g. Steve Ballmer, George H.W. Bush, Michael Ovitz, and anybody slated to succeed Mao Zedong). Executive support can’t make your team trust, respect, or follow you. Only you can do that.

Executive connections are good, but your team comes first.


Executive interaction can be like showing off your rollerblading tricks in front of your son’s friends. If you pull it off, you’re the coolest dad in the school. If you dislocate your shoulder doing a trick, you’ll find yourself alone, fighting to maintain consciousness in the middle of a skate park.

Working with executives can be an asset to your career, but you need to approach it with caution. First, you need to find an executive you trust and who shares an interest in your passion. Second, you need to execute and deliver. Finally, and most importantly, you always have to remember to put your team first.

If you think working with executives is dangerous, in the next post we’ll talk about how to better collaborate with your peers…

Stephen Manley @makitadremel

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