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Deliver first, Challenge Second: The Secret to Managing Your Boss and Getting Ahead

Most people would recognize this scenario: Your boss comes over with a “super urgent” task that he needs you to get onto right away. To you, it seems like a total waste of time and you could do without another “top priority” goose-chase weighing you down. To you, the challenge isn’t managing the task, it’s managing your boss.

Your initial thought will be:

How can I get rid of this extra pain-in-the-ass work?

The Psychology of Why

Something that we all need to varying degrees is an understanding of why a particular thing is needed. It’s what drives companies to spend all that money on vision statements and from a young age it’s the question we are all driven to ask over and over: Why? Why? Why?

According to Simon Sinek, the principle goes even further – he argues that People don’t buy what you do, they buy why you do it. The secret to great leadership and achievements rely on us being able to start with the Why and build up to the What, he argues.

Getting Things Done in Everyday Life

The truth is, many of us as managers or leaders aren’t great at starting with the Why. Our bosses suck at it too. For much of our adult lives we’re forced to push forwards with tasks we don’t fully understand and to stretch ourselves for reasons we don’t fully comprehend.

It is natural and reasonable therefore for us to seek clarification and purpose; to challenge our superiors for a better articulation of Why. The problem, as I see it, is that many of us don’t think too much about how to manage our bosses in a constructive way.

The Problem with Why

In my work I have a hundred things whipping round my head at any given time: instructions from my superiors, problems to solve, future risks to mitigate. As a leader, I always aspire to communicate to my team in a way that inspires them to act and think towards a common goal. As a manager, sometimes I just want them to trust me and get on with the task at hand.

Nothing frustrates me more in a moment of pressure than having to explain myself and my rationale several times to a team member who wants to know “why”. It is frustrating on two counts:

  • It takes time and energy that could be better spent in this moment of crisis
  • It highlights my failings as a leader in inspiring and motivating that individual to attack the task at hand

We could spend all day debating why this probably means I’m a crappy manager, but my point isn’t about my leadership failures, it’s about how challenging for Why from your superiors in a point of crisis could impact their perception of you and your performance. You need to get better at managing your boss.

Deliver First, Challenge Second

If you want to get to the Why with your boss and maintain a reputation as a high-performer, I advocate the Deliver First, Challenge Second model. This model recognizes the following facts:

  • Your leader, however brilliant, really just wants you to get the job done
  • At the point of giving you the urgent task, your leader doesn’t want to spend time “persuading” you to do the work
  • Your leader probably doesn’t want to hear 3 reasons why the job they’re asking you to do is unnecessary (or should be done by somebody else)

What’s the best thing to do in this scenario? Deliver First, Challenge Second.

Deliver First

What do I mean by this? Firstly, get the job done above all else. Doing the job will:

  • Remove the thing that is causing your boss the immediate pain
  • Reinforce your reputation as someone who can get things done

Leaders and managers alike value delivery. Demonstrating that you can deliver consistently will build the level of credibility required in order for you to challenge your boss at appropriate times in the future.

Secondly, delivering the task removes any possibility that your motivation for challenging the task is simply because you don’t want, or are unable to, do it. That you’re unwilling or incapable will be your manager’s first suspicion; Deliver First removes this from the equation.

Challenge Second

Once you have delivered the task to a high standard, you have an opportunity to validate how important and urgent the task REALLY was. The point of completion is an excellent time to qualify the Why with your boss:

I was just wondering, what exactly was it about this that needed doing so urgently?

By Challenging Second, you change the dynamic of the conversation completely. With the credibility of your recent deliverable fresh in both your memories and the immediate time pressures of the urgent task behind you, your boss will be much more disposed to hearing your questions and challenges.

Challenge second will usual result in one of two outcomes:

  • You will come to a better understanding of why your boss needed the task to be done (this will happen more often that you’d like to think)
  • Your boss will come to realize that they overreacted in this instance. Hopefully this will cause them to think twice before pushing the “emergency” button in future situations, but if not then it lays the groundwork for you to challenge them on this in the future when you judge the timing to be right.

The Best Influencers Balance Credibility and Timing

Deliver First, Challenge Second is all about recognizing that there’s a good time and a bad time to be pushing back against your boss and that pressure points are rarely a good time. In addition to timing, you also need the self-awareness to know whether your credibility with them is high enough to land the message effectively.

If you’re in doubt about either the timing or your own credibility then the best thing you can do is Deliver First, Challenge Second.

Brian Djordjevic
About The Author

Brian Dordevic

Bojan is Marketing Strategic Planner with a passion for all things digital. Feel free to follow him on Twitter or schedule a consultation call with him.

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