Are You a “Challenging” or Simply a “Difficult” Direct Report?

Most managers, save for true sycophants, want to challenge their boss.  Few managers want to be puppet yes-people to the boss.  They’ve worked hard to get where they are.  They bring years of wisdom and experience.  They want to push and challenge.  But many don’t know when or how.  More importantly, they don’t know what they don’t know.

How often do you think you’re challenging the boss when he/she thinks you’re just being plain difficult?  Challenging direct reports keep their positions and rise with the organization.  Difficult ones get jettisoned along the way.

There are two great ways you can figure out how often you’re being which:

  • Think of things from the boss’s perspective
  • Ask the boss

Think from the Boss’s Perspective

Bosses want to get things done.  Things generally fall into two buckets:  easy and hard.  Easy things may still entail a lot of work and planning, but there’s nothing really conceptually difficult or unknown about them.

Running the company’s presence at a tradeshow you attend every year might be a lot of work, but I’ll consider it easy for this conversation because that work is known.

Deciding to terminate a problem employee is easy.  (Note inclusion of word “problem.”)  If you see a problem, the adage goes, everyone else has probably already seen it for months and the damage done is more than you know.  This decision is hard from a personal perspective — I’ve never met anyone who enjoys terminating people.  But firing someone who routinely misses deadlines, training sessions, and team meetings isn’t hard in this context.

Launching the new version of a product is easy.  Yes, the positioning may be hard, but managing the overall launch process is easy.   It’s hopefully done a few times per year.  Yes, it’s a lot of work and planning, but there’s nothing conceptually difficult about running the process.

Difficult direct reports make easy things hard.  How?

  • Complexification.  When you ask someone the time you discover that there are three types of people in the world:  those who tell you the time, those who tell you how to build a watch, and those who tell you how to build a Swiss village.  Simplifiers go far in organizations, complexifiers get stuck.
  • Lack of follow through.  Bosses want to talk once about a project, agree to it, and then have it get executed.  As my friend Lance Walter always said bosses want “set it and forget it” direct reports.  If you have a question, come ask.  But otherwise I assume you are tracking our agreed-to objectives and they’re going to happen without me having to check and re-check.  Ditto for feedback given along the way.
  • Drama.  Difficult directs tend to take things personally.  They turn criticism of work into criticism of them.  They view a heavy workload as dramatic sacrifice and not a prioritization problem.  They are sensitive to criticism, defensive when questioned or given feedback, and often unable to separate bad performance from bad intent.

The result is that over time the boss starts to loathe the idea of meeting with the direct report which results in a downward spiral of communication and relationship.

Challenging direct reports keep easy things easy.  They get shit done without a lot of supervision, complexification, or drama.  On the flip side, challengers don’t just go along for the ride when it comes to inherently hard things like fixing a break in the sales pipeline, selecting company or product strategies, or working on a competitive campaign strategy.  They weigh in, sometimes challenging the majority or consensus view.  They provide good arguments for why what everyone else is thinking could be wrong.  Their selective Devil’s advocacy helps the company avoid groupthink and the organization make better decisions.  And they do this without going overboard and positioning themselves as the resident contrarian.

Simply put, when you say something to the boss or in a meeting, imagine how the boss will react and then count the ratio between the following two reactions

  • God, what a pain in the ass.
  • Wow, I hadn’t thought of that.

Ratios above 1.0 indicate you are a net difficult direct report.  Ratios below 1.0 indicate you are a net challenger.

Ask the Boss

Since knowing is always superior to guessing, I’ll give you a set of good questions that can help you figure out where you stand.

  1. If you had to rank your direct reports from top to bottom in terms of difficultly, would I fall above or below the median and why?
  2. Can you please list 3-5 things I do that make it difficult to manage me so I can work on them?
  3. To what extent do you find me difficult/contrarian for difficulty’s sake vs. genuinely challenging ideas and helping the company reach better decisions?
  4. When it comes to strategic debates do you feel that I sit on the sidelines too much, participate too much, or strike a good balance?
  5. If there is a pattern of skipped/cancelled 1-1’s (a sign of avoidance) or higher frequency 1-1’s with other directs, then ask why?

Sycophants know they are sycophants.  Challengers usually know they are challengers.  The risk is that you are a difficult when you think you’re a challenger — and that rarely ends well.  So think about, ask, and take appropriate measures to correct the situation.  Before your boss doesn’t want to talk to you anymore.

5 responses to “Are You a “Challenging” or Simply a “Difficult” Direct Report?

  1. …and those who give you an explanation of the difference between local, UTC and sidereal time.

    That’s a great set of questions, especially 2 and 3. They’re hard to ask. I think that to be really effective in a management role, you need good 360 feedback; and, you need to be able to challenge and push back in many directions as well.

  2. I LOVE this Dave! I have grown a lot since I reported to you and now I manage a lot of people and still think of you fondly. I am stealing this to share with the people I lead. Especially the signifiers of how DR make things difficult….complexification / lack of follow through / drama. Yes. Yes. and Yes.

  3. Kamal Singarapu

    Thank you for sharing your insights, Dave.

  4. Hi Dave,

    My name is Anuj Agarwal. I’m Founder of Feedspot.

    I would like to personally congratulate you as your Kellblog has been selected by our panelist as one of the Top 75 SAAS Blogs on the web.

    http://blog.feedspot.com/saas_blogs/

    I personally give you a high-five and want to thank you for your contribution to this world. This is the most comprehensive list of Top 75 SAAS Blogs on the internet and I’m honored to have you as part of this!

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