Success Rolls Uphill:
Four Steps to Manage Your Boss

By Joe Takash

Conventional business communication has been always been defined from the top down. There are limitless books, seminars and online resources on top down management you can access any time.

However, this is not the case for managing up. Middle management continues to struggle to effectively influence executive management, which is crucial to business survival. Not only should middle managers be able to listen to the problems and challenges of their direct reports, but they should be able to influence a positive change going upward in the organization.

Upward management may be the most important skill set to hone and own, particularity in the volatility of today’s economy. Who better to “have your back” than the boss who is front of you all the time?

The following four-step approach is chock full of nuggets that are simple, but potent. These are not about sucking up or being a “yes” man or woman, rather, these are practical behaviors that require diligence, courage and transparency. You just may find that you’d like to be managed by your direct reports in similar fashion.

Step One: Choose Good Timing: Part of knowing the right timing is setting expectations with your boss upfront, but if you haven’t covered this ground, or the scope of responsibility has changed for either of you, it may be time to realign. Rather than assume what seems appropriate, consider these tips when timing your connections:

  • If you and your boss have travel schedules not conducive to face-to-face dialogue, simply inquire, “When can I get you on the phone for twenty minutes? I’d really like your input.”

  • When you have something heavier to discuss, inform your boss about the importance of the matter. Many employees will try to connect with their boss once or twice and when they don’t get the attention they need, they harbor resentment. While it’s frustrating, chances are your boss is buried with work like you, and availability may be at a premium. Stay on him or her, and be tactfully persistent.

  • Discover the best times for your boss and yourself to speak. Designated times may end up saving time and building strong communication, fueling better results.

Step Two: Understand how your boss prefers information: Perhaps the most common error employees make is they deliver information in the opposite manner that their boss prefers receiving it. This does little to help their connection or personal market value.

A month ago, I gained insight on this topic from my brother who is a partner at a Chicago law firm. He responded, “Some bosses want you to issue-spot, meaning quickly identify the issue you need input on and get to the point. Others want context and background around the subjects being addressed. We’re often accused of not listening, but it poses a challenge when you’re coming to us with the wrong approach.”

So, how does one “know” what the preferred communication is with his or her boss? Eliminate uncertainty by asking so you can provide the highest value on a consistent basis. Other tips to consider:

  • Be succinct and to the point. Even if your boss prefers context and back ground, avoid rambling on.

  • State why you’re coming and what you’re hoping to gain from the encounter upfront. Nothing worse than explaining your situation to your boss and after five minutes he or she interrupts and politely says, “I’m sorry Susan, what exactly can I help you with?”

  • Bring solutions to problems. Sure, you are approaching your boss for answers and feedback, but he or she wants to know you’ve thought it through. The less time they have to spend solving your problems, the more they value your contribution.

  • Do your best to be clinical and emotionally controlled. Often what stands out above anything is your ability to demonstrate passion and confidence, providing you remain cool and in control. Emotional intelligence is key.

Step Three: Align Understanding: When wondering about the perception of his performance, John from New York once told me, “I really dislike the one-time annual review. I need to know how I’m doing more often so I can constantly improve.”

When I asked him what he does about it, he replied, “Every six to eight weeks, I approach my boss and ask him two questions: ‘What am I doing well?’ and ‘Where can I improve?’

John’s approach may be slightly more frequent than you prefer, but it’s so much better than the guessing game that comes with anxiety or fear, particularly in today’s unstable market. A different client inquired about the approach he should take to get into a business development position with his company. I told him, “Approach your boss and tell him you’d like to get into business development and state the value you believe you can provide.” When in doubt, ask.

Step Four: Follow-up and Live Your Word: Few things in managing up are more demoralizing than a boss who doesn’t follow up or get back to you on issues that are important to you and seemed the same to them. This is why it’s critical to capture information in writing during the meeting so they know you’re retaining exchanged data and expect execution. Also:

  • As often as possible, agree on times and dates to follow up on issues discussed so you can diplomatically hold your boss accountable.

  • When your boss can rely in you, loyalty is more likely to be reciprocated. Establish trust through deadline driven behavior and prompt response time.

The road to success upward is one that can be gratifying and rewarding. In a time of uncertainty, it can be a path that is safe and secure. Consider these steps and remember you are judged on your behavior, performance, and results, not on your intentions.

Read other articles and learn more about Joe Takash.

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