Overcoming Accountability Challenges As A Business Owner

by Rachel Steininger

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In this blog post, we will delve into actionable strategies for business owners to build a culture of accountability in professional service businesses and law firms. The implementation of these practical strategies will help you in overcoming accountability challenges while you foster an environment of ownership, high performance, and continuous improvement.

Accountability Challenges for Business Owners

One of the primary challenges that business owners face when handling accountability is the need to hold others accountable without feeling icky or like a micromanager. 

It can be frustrating when asking others to complete tasks and they fail to follow through, leading to a lack of trust and potential resentment. 

Those follow up conversations may feel punitive or be emotionally challenging to tackle.  

Or it can feel disheartening that, when you do attempt to hold someone accountable, you get called out as a micromanager.

Moreover, business owners may struggle with holding themselves accountable, finding it difficult to prioritize important tasks and getting sidetracked by day-to-day operations.

You deserve to have high standards for your business.  And the reality is that your employees might not care as much about those standards as you do. 

As a business owner, you are undoubtedly passionate about achieving your goals and driving your business forward. However, ensuring accountability throughout your organization can be a complex and demanding task.  It may even be one you wish to avoid or wish other people could take care of for you.

At its core, accountability is often misunderstood, leading to frustration, lack of follow-through, and even micromanagement. 

B&W photo of accountability conversation with words "Accountability without the Blech (emoji)"

Understanding Accountability

Before we dive into the how-to of accountability, let’s take a moment to understand the importance of how different individuals react to it. 

Drawing from Gretchen Rubin's book, "The Four Tendencies," we can categorize individuals into four groups: Upholders, Questioners, Obligers, and Rebels. Each group responds differently to external and internal expectations, which can help us understand how to tailor accountability strategies accordingly.

The Four Tendencies Framework


Upholders excel in meeting both external and internal expectations. They have a natural inclination to take ownership, making them reliable and self-motivated.  

Note that this doesn’t mean the Upholder comes with all the skill sets, values, or aptitude that might be needed for the role you’ve placed them in.  But it does mean they will respond well to the expectations set by themselves or by you.

That’s great news for you as the boss, but what about those who don’t respond as an Upholder?


Questioners respond well to internal expectations but not external expectations.  If they decide to do something, they’ll do it.  But if you decide they should do something, it’s not an automatic call to follow through.

From a management point of view, that means a Questioner will often need context or a deeper purpose or alignment before making a full commitment to a task.  They need to make the task their own or have a compelling internal belief or trust in the other person that the expectation is worthy of an internal commitment.

They thrive in an environment that values transparency and provides logical reasoning behind expectations.  And they’ll ask you questions in the attempt to shift the expectations from yours to theirs.

This is a good thing.  It can get frustrating that someone is asking you questions, challenging you even, when you just want them to do the thing you asked them to do.

But giving them context will help the accountability process in the long run. And, if you've set BeyondSMART goals, integrates easily into your overall business growth process.


Obligers respond well to external accountability but may struggle with internal expectations. Think of that person who says over and over that they are going to lose weight, start a new habit, etc. but never sticks to their commitment.

These people are not weak or faulty.  In fact, Obligers often feel a sense of frustration that while so many others are off setting goals and meeting goals, they seem stuck on a vicious cycle of disappointment. 

I also caution your feelings of excitement of having someone so willing to do what you ask of them.  Taking advantage of an Obligers inherent desire to meet others’ expectations can lead to feelings of resentment.  It can take your relationship down the path of 1,000 papercuts without you ever realizing it.

These are the people who benefit from external support and structure to ensure task completion.  Think accountability buddies and regular check-ins.  They will also benefit from your respect and your appreciation of their contributions.


Rebels resist both internal and external expectations, an often frustrating position for you and for them.

Approaching accountability for rebels requires a delicate balance.  Thankfully, this is a small portion of the population but this is a person that will struggle to follow through.  And not just in the work environment.

How To Hold People Accountable

Given the accountability challenges plus our exploration of the Four Tendencies, let’s take a look at some practical ways you can set up accountability in your professional services or law firm without those frustrations.

Blue background with desk accessories.  Overcoming Accountability Challenges as a business owner.
Establish Purpose

Setting expectations (aka asking someone to do something) is not enough.  Effective delegation begins with clearly communicating the value and purpose of assigned tasks. 

To be clear, the purpose is not “because I said so.”  That’s going to take you down a road that’s unproductive in reaching your goals.

Helping share the context means sharing the task in context of business goals.  And not just SMART goals, but BeyondSMART.

Emphasize how each responsibility contributes to organizational goals, to your values, and to the way that you together serve clients.  This will help you engage Questioners to make the task their own.  And also help those with Obliger feel their connection to the organization and a higher purpose, without the resentment.

Reinforce Understanding

Often the issue isn’t even motivation, it’s that the team member never understood the task in the first place or didn’t have the tools to complete it.  

Confirming understanding is essential to avoid misunderstandings and boost accountability.  And whether we like it or not, that will not happen in a single statement.

So before you leave off a delegation conversation, encourage team members to restate their understanding of the task.  This allows you to address any concerns promptly and guide them on the right path before they’ve left the conversation.

It’s also a great opportunity to assess roadblocks that might come up.  Does that person have the resources they need?  The knowledge or the training?  

It’s a simple step and yet it will save you oodles (yes, that’s a technical term) of time in the long run.

Set the Next Check-In Point 

Clearly define the timeline and milestones for each task, including when you or they will next follow up. 

This ensures that check-ins happen at appropriate intervals, avoiding disruptive, spur-of-the-moment inquiries and allowing team members to plan their work effectively.

Side Note: 

A resume will never tell you the full background of someone’s work history, especially when it comes to the personality or work style of their previous managers.  

Just because you’re a great boss doesn’t mean their last boss was.  So when you pop in unexpectedly to call them out on something, their response may be anything from “Great, let’s catch up!” to “OMG I’m about to get fired.”  Seriously.

This could be as simple as “send me an email with the draft by Tuesday” or setting up a meeting time to go through results together.

And just like in the previous step, confirm this understanding so you know and they know what the next steps are, putting you both in a position of empowerment and autonomy.

How To Hold Yourself Accountable

I probably don’t need to tell you this, but as a business owner, leading by example is crucial. It’s time to recognize your personal accountability tendency and seek external or internal support accordingly. 

The vacuum or silo-effect of being a business owner can be overwhelming.  Top that with our brain’s natural desire to slink into a comfort zone and avoid difficult or scary things and you’ve got a big field for procrastination to set in.

So practically, here are some ways to get beyond that.

Make Your Vision Bigger

Want to overcome that amygdala’s call for comfort and safety?  Make your big goals even bigger and more important.  Like adding the purpose and context for your team members, consider who you help by achieving your goals?  Who might you be letting down?

Invest In Yourself

Just like your team member might get hung up on a lack of training, knowledge or skill, so might you.  You were probably trained to practice your craft as a professional or legal services provider.  But business skills, especially the art of business growth and running your business ecosystem, can be more elusive.  

So invest in your own human capital as much as you invest in your business capital.

Get Outside Support

Engaging with coaching programs or peer communities can provide the necessary structure and motivation to meet your goals.  Seeing others taking action or having the opportunity to clear roadblocks with a coach that’s checking in and cheering you on… it can make a real difference in your life and business.

Consider this… our Elite Coaching program has coaching, community, and accountability baked in.  Plus you get the full Acceleration Engine training so you can set goals and meet goals over and over again regardless of your tendency, your team size or your current level of resources.

Overcoming Accountability Challenges

Building a culture of accountability in professional service businesses and law firms is essential for long-term success and growth. These actionable strategies for business owners will help you overcome accountability challenges and foster a culture of ownership and high performance. 

Understanding accountability tendencies, setting clear expectations, nurturing purpose and understanding are vital steps in creating an empowered work environment. By implementing these strategies, you can develop your team and yourself to take ownership, embrace accountability, and contribute significantly to your business's success.

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