Leading Your Leader: 5 Steps to Manage Up and Move Up

road to nowhere

You dreaded this moment, and yet it has arrived. The leader to whom you report has launched another initiative to pursue a new client that has everyone charging down the wrong road. How do you know? You have been down that road before and what you found at the end of it was not pretty. Your manager appears bent on his objective. He also seems to have lost his hearing, not to mention his memory. Worse, people from other divisions are asking questions, “You’re doing what? You’ve got to be kidding!”

You asked your boss in a tentative voice, “Uh, didn’t we try this approach with the Zephyr Group?” What you didn’t go on to say is that your company not only ended up losing the deal but the client as well, who felt their time had been wasted.

Your boss waved his hand dismissively. “That one was completely different. This is a different company, team, and project.” He then shot out the door.

He is right. Zephyr was a different company, team, and project, but the fatal flaw is the same. There is a cheaper, off the shelf software solution out there that would work for them without the hassle and expense of working with your company. This is no great mystery. Why is your boss unable to see that?

The Challenge of Dealing with a Challenging Leader: 

Dealing with issues caused by an ineffective leader who happens to be your boss occurs all too often in organizational life. It shows up in a variety of ways:

  • Requests for approvals that go into a black hole.
  • Lack of clarity on a vision for your division that makes it hard to know how to prioritize your time.
  • New initiatives are started that conflict with the goals of existing ones.
  • The pursuit of a bright shiny object today and tomorrow it falls off the list.

When you are starting out in your career, dealing with the chaos of an ineffective leader is stressful, but you regard it as a growth pain of professional life.

That changes as you gain experience and evolve into your own leadership role. The bad behavior of your boss not only compromises your effectiveness as a team, but it also can have a longer term impact on your own leadership brand. You can get tarred by his or her brush, being viewed as part of the problem, not the solution.

You can always elect to leave the company, but the cost of leaving a business, colleagues, and place you have accrued valuable experience might be higher than remaining there. Further, sad to say, ineffective bosses appear in every company. Unless your company has many bad bosses, which points to a major cultural issue, try solving your current situation in a way that will help your career and leadership brand. It will require you to plunge into new places, but the reward could be good for you and your organization.

Five steps for managing a difficult boss and your leadership career:

  • Don’t personalize your boss’s behavior. The abrupt response your boss gave you was not about you. More likely it comes from his own insecurity that he does not want to face.
  • Figure out what problem you need to solve. Do some detective work to learn what you do not know about this situation. That means sleuthing for reliable and trusted information sources and asking some awkward questions. Does your boss have a relationship with the targeted new client he wants to leverage? Is there pressure from senior leadership to get more proposals out as part of a performance metric for business development? Did something happen in the market with the off the shelf software package that has made it less desirable?
  • Create a repositioned plan: If what you learn is anything other than your boss was right, create a new plan to solve whatever issue you discovered from your sleuthing.  Find a way to position the plan in a way that does not implicate your boss and seeks a broader business issue. For example, the issue your company encountered with Zephyr may signal a shift in the market that it would behoove your division to research.
  • Find others to influence the outcome: Find others inside your organization who can influence the outcome because your boss listens to them. To get their buy-in, create a message that is not personal to your boss but emphasizes the broader business issue. For example, “We are finding our services competing with an off the shelf software product. We need to spend time evaluating the current market and how it is changing to know what we should provide. It might require refreshing and updating our offerings, which could be great for us and for them.” Then agree with them as to how and when to talk with him.
  • Sell your plan to your boss: Choose an approach with your boss that fits his communication style. For a driver like the boss in this story, make sure your message is concise. “Hey, in working on this new deal, I’ve come across a bigger opportunity that could make this and other deals work.” Be prepared to either line out your three top points and recommendations in the hall or arrange to sit down with him to make the pitch and plan new action. With a proposed win for both of you and the help of the other influencers greasing the skids, you will help your organization and your leadership career.

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