Clarity in leadership

Written by Briana Cavanaugh

November 22, 2021

Clarity in leadership

You may know that I love to talk about the importance of getting clarity within yourself and getting clarity in your business planning. Values and goals plus great bookkeeping gives you the information you need to make great decisions! Today I want to talk about getting clarity in communications with your experts.

We all have miscommunications sometimes, so how can we get to the best decision when things get weird?

While my main goal right now is to directly benefit your decision-making, this will have a couple of side benefits. For one thing, you’ll improve your relationships with your experts as they will know that you appreciate their expertise. For another, you’ll be able to give them clearer directions, which will help them know where they stand and how they can best help you.

Who are your experts?

Your experts are people who know more than you do about something. They’re people you chose to be your contractors or employees to help you meet certain goals for your business.

The obvious examples are service providers such as your employment law attorney and your CPA, who have deep qualifications in specialized and complex domains.

But there are all sorts of experts we work with. People who couldn’t afford college can be experts, too, especially when we understand that our ability to even recognize expertise has been distorted by the Eurocentric bias of our school system.

If nothing else, a person is always the world’s best expert on their own experience. Suppose you hired a virtual assistant fresh out of school and taught her everything she knows about how to do your administrative work — she’s still in the best position to tell you what she did and why. Your employees are your experts, too.

And in independent contractor situations where you trade business services with another entrepreneur, you might take turns being the expert for each other!

So let’s look at what to do when the expert tells you something that seems incorrect, or the expert is repeatedly trying to draw your attention to something that seems irrelevant.

Pushing my point of view versus pulling theirs forward

When I’m paying someone, sometimes they feel pressure to do as I say even when they disagree.

It’s even possible for some business owners to push their experts so hard that the expert obeys when the entrepreneur gives a direction that might expose the business to liability for civil penalties!

Getting pushed this hard can be demoralizing for an expert — many people pride themselves on doing their job well, and my experts don’t want to bring negative consequences on my business. And of course, I don’t want the negative consequences, either.

To navigate to the best decision, it’s important to make room to collaborate. That can mean that I need to encourage my expert to talk more, by asking questions and using my active listening skills.

Look for inner barriers to communication

Everyone has inner barriers. You and your expert might each be getting tripped up in these barriers at the same time.

Is the expert hesitant? When a person disagrees with me hesitantly, that can add fuel to my belief that I’m the correct one.

The reality is that expert opinions do not always sound absolutely certain. This can actually be a reflection of how deep their expertise goes — they’re seeing a nuance or branching point that’s based on some factor I’ve overlooked, or they are prudently re-examining their point of view in case they’re mistaken.

Differing opinions can also come from a difference in values. Everyone is unique and prioritizes things differently. A difference in values doesn’t mean that anyone is a bad person or that this expert cannot work for you. It does mean that sometimes they have to reshuffle priorities in their mind so that they can better serve your values and goals, which can slow down how they express themselves to you.

Did I miss something? Did you miss something?

Asking your expert questions can clarify whether you’re both on the same page. Sometimes when a conversation gets confusing, it’s because you and your expert were actually talking about two different things entirely. It might be necessary to backtrack.

“Did you handle the client’s complaint?” you might ask, unaware that your question is ambiguous because there was a second client complaint that your expert has just finished smoothing over.

For another example, is the tax that your expert mentioned supposed to be paid by you or by your clients? Is this IRS form supposed to be about your status when you work for your clients — or is it about the status of your subcontractors and vendors when they work for you?

Sharing expertise

Sometimes I have to check myself. Am I sure I know more about this subject than my expert does?

A business owner does have a relevant area of expertise, too — you’re the expert on your business. If you know or suspect your expert is overlooking something, or if you aren’t sure you’ve informed them of something, it may help for both you and your expert to move to a place of curiosity.

This gives you both the space to unpack the reasoning that brought each of you to your conclusions. “I thought that because my business is such-and-such entity type, I don’t have to file that form. Can you explain more about that?” This is a great way for each of you to learn relevant information.

When I encounter a disagreement with someone, my first reaction might be to feel annoyed and defensive. If I stay with that, I tend to cling even harder to my opinion, which makes it all the harder to navigate to the best decision.

When I move to a place of curiosity, I never know where it will lead. In the end, we might find a solution that is better than either of us could have come up with alone.

Honor your feelings

Sometimes we resist advice because part of us just doesn’t want to be told what to do. That part of us may be a big reason why we wanted to become an entrepreneur!

I’ve also struggled with shame or defensiveness because I didn’t already know what my expert told me, as if I’m supposed to know everything in the world. Or I feel ashamed because my expert told me this before and I forgot.

We may get these feelings from our personal history with school, if we had authority figures who treated us with scorn for having a beginner’s mind.

When I encounter this kind of reaction in myself, I know that my reactions are about the healing I need. I know I need space to heal and love my past self — and I also know that these scars can make it hard to hear wise advice from my expert.

Understand the risks & timeline

Depending on what the disagreement is about, the consequences of making the “wrong” decision might not be terribly high.

A disagreement with a logo designer about whether an orange or red logo is better — well, maybe that’s not very important. My web and art design team is fantastic and I trust them a lot, but I also want the results to be pleasing to me. So if I’m sure it’s just a minor matter of taste, I might tell them to just do it the way I want.

On the other hand, if the web designer tells me it’s really hard for my clients and potential clients to find what they’re looking for on my website because of the way the menus are organized, that actually is important! Companies lose business over that kind of thing.

And my tax expert’s whole job is to worry about things that could involve even bigger losses than that!

Another question I ask myself is whether it is important to resolve this disagreement right now. If I’m confused about my tax expert’s advice, I don’t always need to get clarity before the end of the meeting.

Resolve it later

If the issue isn’t urgent, I might ask my expert for a search term that I can Google, or I’ll ask for the expert to send me an email with more information about the topic, so that I can educate myself at a better time.

Get a second opinion

When disagreements with your expert are frequent, or the potential consequences are serious, I might check with another expert for a second opinion.

Value the relationship

I have sometimes come away from a disagreement with the realization that I can’t work with this service provider any more. That’s valid!

Much more often, I still value and enjoy this person and their expertise.

But did I tell them that?

It’s easy to forget to give positive feedback, especially when things are going smoothly. Our experts don’t follow us around all day, so they don’t know how much we’re thinking about and making use of their advice — unless we tell them about it!


Having a team of experts is lovely! Here at bookkeeping company Bliss Your Money, I prompt Team Bliss to express appreciation for each other, celebrate their wins, and talk about their accomplishments every week at the staff meeting. Let us help level up your business so you can build your own team of experts!

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