Art of the Compliance Ask, Part One: How to Get What You Need Without Becoming Everyone’s Least Favorite Person

Let’s face it, when you are a healthcare compliance officer, eventually, you are going to have to ask an operational leader to do something they may not necessarily want to do (e.g., a concession with a proposed business deal, completing a training, reviewing a policy).

And from time to time, you will have to tell someone that the super-efficient process they developed last year, unfortunately, exposes the organization to risk because it doesn’t align with an existing policy or regulation.

(Good times.)

Nevertheless, these are also moments when the art of the compliance ask comes into play, where the goal is to influence the decisions of others, when you lack authority, and without creating unnecessary resistance.

One of the best skills for accelerating a compliance career is knowing the most effective way to ask an operational leader to do something they don’t want to do. This is the first in a two-part series exploring practical strategies for making those asks in a way that gets results without creating unnecessary resistance.

Learn to Ask Questions Before Making Recommendations

When it comes to working through a potential compliance issue, it’s a natural tendency to want to jump in and make a recommendation. The problem with that approach is that all compliance issues involve context (i.e., “the why”), and without fail, certain facts and circumstances aren’t known unless you work to identify them.

So, before making any recommendations, ask questions to make sure you understand the context surrounding the matter you are working on. The exact questions you need to ask will vary, but here are some basic ones you can start with:

  •  “Help me understand _____.”

  • “What problem are you trying to solve?”

  • “What does life look like for your department (or staff) if we’re not able to achieve the result you’d like?”

When you take an approach that leads with questions, you are taking an active interest in your leader and seeking to find a solution that will actually work. This will be evident to your healthcare leaders and help you earn their trust and respect. Lastly, keep in mind that the more you understand their operational objectives, the better positioned you are to make a compliance recommendation that is successful.

Always Include Context

Piggybacking off the above strategy, let’s continue to explore “the why”, but this time, let’s focus inward on your messaging with the compliance ask. Whether the content of what you’re talking about involves delivering education, investigating an issue, or conducting an audit, everything you work on has context around it.

 Everything.

(And I say that as someone who isn’t a fan of communicating in absolutes, but in this case, I need to make an exception.)

Sometimes referred to as, “the why”, providing context helps your leaders understand the reasoning behind your message that compliance matters. For a compare and contrast, consider the following example:

When you include context in your compliance ask, it makes the communication much more effective because you are directly appealing to your leaders’ interests, sense of responsibility, and aligning with the organization’s mission and values.

Make the Ask Collaborative

When it comes to presenting a compliance ask, let me say this upfront. The ask that stands the best chance for success is the one that sounds less like a demand, and more like an invitation to solve a problem together.

For example, imagine you discover that a department’s current process creates a compliance risk. You could tell the department leader, “This process needs to change.” Or you could say, “I understand why the team is using this process, and there is a compliance risk that we need to address. Can we look at a couple of ways to solve the issue while preserving what is working for your team?”

When you make the ask collaborative, you’re creating space for the operational leader to participate in a discussion about solving a problem, instead of shutting it down. In my experience, people are generally more committed to compliance when it involves solutions that they helped develop vs. being told what to do. 

Give Them Options Whenever and Wherever You Can

Another way to increase the likelihood of success with your ask is to avoid presenting every compliance issue as an all-or-nothing decision.

Yes, there are times when there is only one acceptable answer, but in many situations, there are multiple ways to reduce or manage the compliance risk, and these should be explored first when making an ask. For example, instead of saying, "This is what you need to do," present options such as: "The way I see if, we have ___different ways that we could address this.”

The reason giving options is important is because it demonstrates that you've thought beyond identifying the problem. It also, gives the leader a sense of control, which improves your chances for their engagement.

When you take this approach you are changing the landscape of the conversation because you’re not telling the leader which option to choose, rather, helping the leader make a business decision while explaining the risk implications of each option. That will improve your chances for success and change their perception of you from obstacle to trusted advisor.

Pulling it All Together

One of the unwritten rules of compliance is that you are rarely the person actually making the decision. You can identify the regulation, explain the risk, and even have the perfect solution neatly outlined, but you can't force another human being to make the decision you want them to make. (If only compliance came with a remote.) What you can do is influence how that decision gets made, and that is where the art of the compliance ask comes into play.

When you follow the above strategies and develop this skillset, something noticeable will happen. Your operational leaders will stop seeing you as the person who tells them what they can't do and start seeing you as the person who helps them figure out what to do.

I hope this information was helpful. If you try any of the above, please reach out to me. I would love to hear how it went. You can shoot me an email at janstine@bluebirdhealthlaw.com.

Stay tuned next month for part two of this discussion...


The art of the compliance ask is exactly the type of thing that I coach students about inside my interactive course.

If you want to accelerate your career and become a trusted advisor to leadership, then look no further.

We’d love to have you join us inside the course.


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