Resolving issues with your boss without being a nag

Jonathan Mills
3 min readApr 22, 2019

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You’ve asked your boss to assist you in resolving an issue — he said that he would, but it remains unresolved. You’ve asked him again — he mentioned that he has been too busy, but that he would do it. You have smiled at the boss in the corridor and mentioned it again: “Hey Sam (the boss), don’t forget my issue!” and he smiled back and grunted that he hasn’t forgotten. It has been weeks now, but Sam has not yet found a suitable solution. Do you just shrug your shoulders and move on or is there something that you can do to stimulate action (without nagging)?

A few important points need to be born in mind here — people (yes, even managers) procrastinate or shy away from doing things for the following reasons:

  • Blurred vision — not understanding how the pieces of the business fit into the strategic imperatives framework
  • Fear — insecurity and anxiety hamper decision-making attempts and put a brake on progression
  • A lack of self-belief — misunderstanding of giftedness and a poor self-image immobilise talented people
  • Avoidance — procrastination frequently occurs where the steps that need to be taken to advance are difficult, unpleasant or tedious
  • Stress — an overloaded schedule, panic as a result of adverse circumstances or dysfunctional relationships all can lead to inactivity and putting off essential tasks

Taking these possible reasons into account when addressing inactivity on a request that you have issued to your boss and attempting to be sensitive to your boss’s context, have a constructive conversation with the boss requesting progress feedback on specific milestones, for example:

“Hi boss. I am frustrated with the seeming lack of progress that we are making at resolving the repair of our machines (note the use of the inclusive “we” in this sentence). They are breaking down all too frequently and thus hampering our ability to get product to despatch in a timely manner. I am not sure that we will be able to reach our targets this month unless something gets done to provide us with reliable tools”.

(Now, the boss may answer in a variety of ways, but the answers typically fit into one of two possibilities — answer accordingly)

You: “Thank you — that’s good news. Yes, let’s develop a contingency plan together”.

You: “Yes, these machines are certainly a big budget item. At the same time, however, our customers are starting to complain that their orders are not “on time and in full” (OTIF). They are starting to question our reliability as a supplier. May I develop an impact study that you can take to the Finance Director — a study that outlines the waste we are experiencing and related costs, besides the obvious damage to our brand reputation?”

Boss: “Yes, thank you. That should help”.

When encountering inactivity from your boss in response to a request for action, handle the situation firmly, but sensitively. Nagging doesn’t help. The idea here is problem resolution and not putting your boss down or “on the spot”.

Originally published at https://www.stretchforgrowth.com on April 22, 2019.

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Jonathan Mills
Jonathan Mills

Written by Jonathan Mills

Jonathan has spent over 30 years focusing his efforts on developing people throughout the world. He believes that people have the most impact when stretched.

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