Want Improvements? Help Your Boss Feel Safe Enough to Try the Better Way

It can be quite startling to recognize how often leaders and other people with authority and status behave ineffectively. Their difficulties can be interpersonal, as when a leader shows favoritism to specific individuals or groups through job assignments, compensation, or simply by taking them out for drinks while neglecting others. 

But it’s even worse when someone with hierarchical power is a poor decision-maker and causes an organization unnecessary expense because they can’t see what needs to be done to improve results. (And I’m calling myself out here, because I can procrastinate terribly about deadlines, creating unnecessary bottlenecks and other complications for members of my team.)

When you work for a problematic boss—and there are hundreds of other examples, unfortunately—how do you talk to them about the problems? Sure, it’s uncomfortable to think about having the discussion, but wouldn’t it make more sense to share your observations with your boss rather than just gritting your teeth and working around them day after day? 

Who’s Best to Speak Truth to Power? It May Be You

Perhaps there’s someone else in the organization with skills or expertise who could take over what the leader is doing, or at the very least, supplement their activities. Or maybe there are other work methods that could produce better outcomes for the entire team, if only your boss would accept them.

It’s a very big ask for employees who don’t have hierarchical authority, clear direction, or support to have to find and implement a better way on their own. Speaking truth to power carries real risks for you as an employee—from experiencing the emotional sting of having your advice and recommendations rejected to losing your status, close relationships, or actual job. Plus, your decision to take action will depend on many factors, from assessing how big the penalty will be if your boss doesn’t accept your input to the fact that, despite all your efforts, your boss may still never get their act together. 

So can you actually help your leader feel safe enough to experiment with doing things in a new way? For your boss, your proposal may only look new and different, not better. The idea of change can feel risky and frightening, even if you’re confident it will get improved results—the kind they say they actually want. The trick is to help your boss feel safe enough that you can activate their drive for the preferred outcome. So try to provide a kind of scaffolding for how a change experiment might work, rather than focusing on their current, negative processes and behaviors. 

Is There an Alternative to Your Change Initiative?

Sometimes a boss doesn’t know what they don’t know—and no one has the heart to tell them. In that case, you may be the person with the courage to have some exploratory dialog with them, offering alternatives to whatever is going wrong. But first, assess your own risks.

What might happen if the leader doesn’t make improvements? Perhaps other good employees will turn over. If customers continue choosing competitive offerings, there will be less money available for growth, including for your own and your colleagues’ compensation. Or what if business is okay, but some of your values are being violated—and besides not feeling proud of yourself, you feel embarrassed in front of your team members because you appear to be supporting bad values

And what’s likely to happen if the change initiative you’re proposing doesn’t work? Even with new branding, customers might not buy more; despite better working conditions, employees may continue to turn over; and though corporate diversity and belonging efforts could improve, there may still be values violations.

Build on Small Successes 

After you’ve considered your risks, if you still feel motivated to go ahead and have that talk, concentrate on giving your boss a sense of control. They’ll need this to feel safe as you encourage them to accept that things are going to change. Hold plain and simple conversations to review the data associated with improved outcomes vs. current outcomes. Decide ahead of time how you’ll ask about how they feel things are going and which current conditions they want to preserve. 

As you explain the experiments you want to try, give your boss as many opportunities as possible to set the parameters for when things will happen and to what extent. Pacing, frequency, timing, and volume may matter. Emphasize the benefits of any and all improvements rather than focusing on the less satisfying past. This will help you avoid sounding blameful, which could cause the boss to withdraw.

Remember, we’re talking about dealing with a problematic boss. If you’re lucky enough to have an excellent relationship with a thoughtful, future-facing boss, you may not need these kid-gloved approaches, although the premise of offering data and providing a comforting amount of control should be reassuring to anyone. But if your boss is ineffective, try to start with small initiatives that have a high likelihood of paying off. Some early successes will let you build your credibility and minimize your boss’s discomfort. And if there are bigger risks you’d like to take over time, it’ll be even more important to build up from a base of wins. As in many things, when you’re trying to help an ineffective boss shift their attention and involvement, success breeds success.

Onward and upward—

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