Negotiations: Managing up


Three months ago, I was assigned to a new boss. He’s often slow to respond to my requests and can be difficult to track down. This week, I almost lost two big deals because it took days for him to get back to me with an answer. He’s becoming an impediment to my business success. How do I approach him to negotiate a more productive working relationship?


Sadly, when we accept a position with a company, we can’t predict the trajectory of our career or who we will work for along the way. Your experience is an unfortunate but common occurrence in U.S. business. A recent study published in Human Resources Executive magazine showed that a third of U.S. employees are dissatisfied with their boss and a Gallup poll estimates that costs U.S. businesses $360 billion annually. I wish there was a simple solution.  

In my opinion, you have three options:

  • Initiate change. Try to retrain your manager.
  • Tolerate. Make the best of a bad situation.
  • Leave. Find another job or another position within the company.

Option 1: Initiate change

This is the preferred initiative but realistically speaking, one that requires a lot of effort and may produce little in return. Most “high maintenance” managers like who they are and in fact, choose to be that way, for reasons they may or may not be consciously aware of.

Be mindful that it’s highly unlikely your manager will change and even if he does try, the odds are against him that he will be able sustain it. I don’t want to discourage you, but simply prepare you. To improve this relationship, consider these steps:

Set clear expectations. High performance begins with clear expectations. Both the leader and employee must be clear about performance standards, understand what is expected and how success will be measured.

Meet face-to-face. Especially if your boss travels a lot, schedule time to meet with him. Let him know in advance that you want to talk with him about some ideas you have to better support him and the company. This will prepare him for a strategic conversation rather than the typical, “Here’s what I need from you” conversation.

Prepare. In advance, write the questions you want him to answer and gather the information you’ll need to support your ideas. Dedicate the same time, attention and  detail to prepare, as you would if you were meeting with a top 10 customer. Practice how you will open the conversation, which questions you would ask first, second and third, and how you will redirect the conversation if it digresses. You might need to say to him, “Howie, that’s an important subject. I’d like to address that after we finish _____.  Are you okay if we put it in a holding pattern for a few minutes?”

Take notes. Capture the key ideas and agreements from your conversation. This will help you recap the conversation when you send him an email.

Also jot down his key phraseologies. When you communicate with him and use words that he’s comfortable with, he’ll feel like “it’s really easy to talk with you.” You want to create as many bridges as possible.

Communicate. Effective leaders create a forum for two-way communication to flow. Unfortunately, your leader is not an effective communicator so you will need to initiate communications with him.

When you do so, keep your agenda short and on point. List your key discussion topics in bullet form and present them in a similar fashion. Tell him what you need him to do, when your deadline is and then let him talk. Before you conclude your conversation say something like, “Howie, I know your schedule can go sideways very quickly and the demands of this business are daunting. If I don’t hear back from you by 4 p.m., what do you want me to do? Call you? Tell the customer/employee . . . ?” This way you have an agreement in place that he pre-approves regarding you should handle the situation.

When you find that you need to track him down to get an answer, leave messages everywhere  – on his voice mail, cell phone and send him an email and be courteous when you ask him to reply. 

Be accountable. Take responsibility for your actions and those of your team members.  Stay on top of your business so he doesn’t find it necessary to get involved. 

Your list of performance expectations can be the conduit to keep the lines of communication open. When you’ve taken the initiative in a specific area, send him a short email to report the action you’ve taken and results. If he’s smart, he will realize that you are doing his work for him and that he can take all the credit. Over time, this may help you gain his confidence which may improve how quickly he responds to your requests.

Option 2: Tolerate

You may outlast your manager. The tour will be difficult. You can expect there to be landmines and ravines. You will need to dig in, practice emotional discipline, have patience and find creative solutions as the situation warrants. Given time, you will develop strategies for coping and may learn how to push his buttons in ways that effectively elicit a response. An occasional shot of scotch or 1 lb. box of Godiva chocolates might help you endure the wait. 

Option 3: Leave

If you decide to leave your company, don’t jump ship too quickly. The grass may be greener, but then again it may not. Emotional decisions made too hastily can backfire. 

If you decide to leave, complete your due diligence. When interviewing prospective employers, ask questions to learn what values support their business success. For example, I might ask, “What is the acceptable turnaround time for a manager to respond to a direct report who requests pricing terms for a negotiation.” Anything greater than 24 hours should raise a red flag that the company lacks a sense of urgency.

It’s also important that you define the type of relationship you want with your immediate supervisor. Specifically, what do you need and want from this person? For me, feedback – both reinforcing and development – is a “must have.” I need to have the freedom to talk about anything that impacts the business positive or negative. Our agreement should be that we always demonstrate sensitivity in how we talk to one another, but that any topic is game.

When I worked for Slim-Fast Foods, I was contacted by a headhunter who represented Nabisco Biscuit Company. After two initial interviews, I was lukewarm about the company. But in my third interview, I met the manager who I would report to and he knocked my socks off. I knew immediately that not only did I want to work for him, but also, that he would impact who I was as a leader in the best possible way. I was not disappointed. Today, I am grateful that I availed myself of the opportunity to sit along side of him to learn, test, fail and relearn. He was a brilliant coach. It was one of the best decisions in my life.

I wish there were a simple solution to dissatisfaction with a boss. When it comes to changing someone else’s behavior, the law of averages is unfortunately stacked against you. Sometimes we are forced to experience a situation that is very uncomfortable or distasteful because the lessons we learn about ourselves and others have far reaching benefits at a later time in your life. Only you know what option is right for you. Good luck.

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