Steps for Presenting Problems or Opportunities to Your Boss

Did your project come in $10,000 over budget? A rival poach your star performer? Your competitor beat you to market with a new product? None of us likes to deliver a difficult message, but it can be a valuable tool for building a trusting relationship with your boss. You know that you should never bring a problem to your boss without a proposed solution. But often we forget to frame the situation in a way that helps us garner the necessary resources or approval to begin moving toward a solution. Here are five steps to take the next time you need to deliver bad news—or a promising opportunity.

1. Describe the problem or opportunity to your boss. Provide a general overview of the problem, and show the specific impact it has on your work and the company’s goals. If you’ve identified an opportunity, show the potential benefits—not just to you or your team, but to the larger organization.

   “Stu, we’ve got a morale problem on our tech team. Our recent employee survey shows that 40% of our staff in Atlanta doesn’t find their work rewarding or challenging. If we don’t address this, we might lose some of our best talent. We can’t afford that at any time, but especially now when we’re trying to release the new system by Q1. I have a few ideas I’d like to try, with your help and the cooperation of HR. I think with the right approach we can keep the team focused on meeting the Q1 goal.”

2. Identify your solution or approach. Explain how you’ve already tried to solve the problem and what you’ve learned from those attempts. Recommend a specific approach, along with alternatives, to provide your manager with options.

   Clearly define each possible option, addressing the pros and cons, and any potential risks or barriers. Explain the logic behind your recommended approach. You want your manager to be aware that you’ve considered several possible outcomes.

   “It looks like we’d need to add two more managers to the project to meet the client’s latest round of requests. When I mentioned this to Sarah during our conference call, she didn’t respond. I’d like to go to Cincinnati and meet with her to discuss how we might renegotiate the contract. I think seeing her face-to-face will make a big difference. Plus if I do it the week after next, we’ll have just delivered on the second phase of the project and she’s likely to be pleased. We could of course take the hard line and just say no to their requests and then see what they come back with. But I’m afraid we’d be putting our future relationship at risk. We could also just expand the team and do the work and see it as a marketing investment. We’d likely win Sarah’s good graces and, as you know, she’s well connected with many companies in our target group. But it may be more financial risk than we’re willing to take on right now.”

3. Explain the implications. Consider the impact that your proposed solution will have on yourself and others, including your manager. Be explicit about how your idea will have far-reaching effects on the goals of the organization.

   “If we put a formal process in place to track all sales leads, I can do a better job of connecting the dots between the VPs who are meeting with potential customers. As you know, the current approach worked well when we just had two VPs doing the calls, but now we have over 20. This will increase their workload slightly, but it will be clearer to them how to share lead information. It will also give senior leadership a better view into the pipeline. It won’t take a week to pull together our sales dev reports, which means you can be more responsive to requests from above.”

4. Discuss the benefits. Focus your conversation on concrete examples of your idea’s benefits. The specific features of the solution, or how it will be implemented, are less important at this stage. If you have tested your approach on a small scale with good results, share that information.

   “Delivering the product in a smaller container in the Latin American market will expand our customer base. We’ll be able to serve truckers with small rigs who go on long hauls but don’t have room for the 20-gallon containers. Most of these truckers haven’t bought our products before, so we have the opportunity to convert them to our brand. They’ll also be able to pay cash, since the smaller container will be at a lower price point. This is a real advantage in their cash-heavy economy. Carlos helped me run a quick experiment with a small set of truckers in Panama, and the response was overwhelmingly positive.”

5. Accept responsibility for the outcome. Demonstrate your commitment to ensuring success. Work with your manager to develop a final action plan for taking advantage of the opportunity you’ve presented.

   “This rests squarely on my shoulders. In the unlikely event that we don’t convert enough customers from this campaign, I’ll quickly move on to Plan B. But to get started I’m going to reach out to Terry to get the e-mail list of current customers who have opted-in. Then I’ll work with Ellen to draft the e-mail pitch. Once I’ve done that, I’d like to get your help running it up the flagpole. Does that sound like a sensible plan to you?”

Adapted from Managing Up (product #14784) from the Pocket Mentor series, Harvard Business Review Press, 2008