Episode 105: The Conversations You’re Avoiding Are Costing You: How to Have Tough Talks with Your Team

Feb 19

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Conquering Workflows & Systems for Bookkeepers & Accountants podcast with Alyssa Lang, founder of Workflow Queen and Magnetic Profits. Episode topic: The Conversations You’re Avoiding Are Costing You: How to Have Tough Talks with Your Team.

In this solo episode, Alyssa Lang covers the intricacies of handling difficult conversations within your bookkeeping or accounting practice. Alyssa breaks down practical steps on preparing for hard dialogues, using data-driven approaches, and creating impactful outcomes, ensuring you nurture not only a productive team but also foster personal growth as a leader!

In this episode you’ll hear:

How to prepare for hard conversations with your team using a step-by-step framework
Why hard conversations are essential for avoiding business bottlenecks and fostering growth
What steps to take to evaluate the root cause before having a hard conversation
How to use data and KPIs instead of emotions to guide tough discussions
What performance improvement plans entail and when to let someone go

Resources mentioned in this episode:

💻 Breakthrough for Bookkeepers & Accountants

⚙️ Notion

👉🏼 Sign up for The Removable CEO Workshop on February 25th @ 12pm EST!

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Are there conversations you're currently avoiding in your business because they feel too uncomfortable? If so, they’re probably the exact conversations you need to have to grow and scale.

Whether it’s addressing underperformance with a team member, setting boundaries with a client, or even confronting your own leadership struggles, avoiding tough discussions only leads to frustration, resentment, and stagnation.

Here’s the thing: Most of the time, we’re not avoiding these conversations because we fear confrontation. We avoid them because we don’t have a clear plan for what we actually need to say or how to navigate them effectively.

In this post, I’ll walk you through how to prepare for and navigate difficult conversations with your team using a step-by-step framework. If you’ve been dreading a conversation, this is for you.

Personal Story: My First Hard Leadership Conversation

I get it. These conversations are tough. The weight of leadership can feel overwhelming, and I’ve been through this plenty of times. One of the hardest conversations I ever had was when I realized a team member wasn’t meeting expectations. My gut reaction? Just let them go. But I paused and reflected…was this a hiring mistake, or was it a failure on my part as a leader?

Instead of immediately firing her, I made a bold decision: I put her on a two-week paid leave and rebuilt our onboarding system from scratch. When she returned, we essentially re-onboarded her as if she were a brand-new hire.

The result? She became one of the strongest assets to our team.

That experience taught me that hard conversations aren’t about placing blame; they’re about creating clarity and setting people up for success.

The Cost of Avoiding Hard Conversations

When we avoid these discussions, here’s what happens:

Poor Performance Continues – If an employee isn’t meeting expectations, and we never address it, we enable mediocrity in our business.
Misalignment Grows – The longer we let things slide, the harder it becomes to maintain a business that aligns with our values.
Small Issues Turn Into Big Problems – What starts as a minor issue (missed deadlines, lack of initiative) can turn into major inefficiencies that hurt profitability and client satisfaction.

If you’ve been dreading a conversation, this guide is for you. And if you’re serious about stepping into leadership, join us for The Removable CEO Workshop on February 25th @ 12pm EST, where we’ll help you implement these leadership strategies in your firm.

5 Steps to Navigating Hard Conversations

Step 1: Evaluating the Root Cause Before the Conversation

Before jumping into a tough conversation, take a step back and set your ego aside. Ask yourself:

Is this an issue with their performance, or did I fail as a leader to set them up for success?
Have I set clear expectations? If you hired a team member but never documented what success looks like, how can they meet your standards?
Did I provide the right training, support, and systems? Inside Breakthrough for Bookkeepers & Accountants, we teach leaders how to structure onboarding and training using Notion to ensure team members have what they need to succeed.
Am I reacting emotionally, or do I have data to back this up? This is where tracking KPIs comes in handy.

Once you’ve evaluated the root cause, you’ll be able to approach the conversation from a place of clarity rather than frustration.

Step 2: Preparing for the Conversation

Nothing is worse than walking into an important conversation without a plan. Preparation is key to keeping the discussion objective and productive.

Here’s what you need to do:

Get clear on the facts. What specific examples or data points illustrate the issue?
Review KPIs and performance metrics. Using Notion to track team KPIs keeps everything black-and-white rather than emotional.
Decide on the goal of the conversation. Are you coaching them to improve? Setting clear expectations? Or is this a discussion that may lead to letting them go?
Consider their perspective. What obstacles might they be facing that you’re unaware of?

With a clear plan in place, you’ll feel more confident and in control.

Step 3: Leading the Conversation With Confidence

When you finally sit down for the conversation, approach it strategically:

Be clear and direct. Don’t sugarcoat the issue, but also don’t attack them.
Use data, not just emotions. Saying “I feel like you’re not performing” isn’t helpful. Instead, say, “Over the past three months, we’ve tracked errors in your work, and your accuracy rate has been 70% instead of the expected 95%.”
Allow space for their response. They might have insight into challenges you hadn’t considered.
Focus on a path forward. What needs to change, and how will you measure improvement?

If the goal is to help them succeed, outline the next steps with a clear timeline.

Step 4: Implementing a Performance Improvement Plan (If Needed)

If your team member has potential but isn’t meeting expectations, consider a Performance Improvement Plan (PIP) instead of letting them go immediately.

A PIP includes:

Clear expectations for improvement
A set timeline for measurable progress
Weekly check-ins to assess performance

Inside Breakthrough for Bookkeepers & Accountants, we provide a customizable Performance Improvement Plan template so you can easily structure these discussions.

A well-structured PIP ensures there’s no confusion about expectations, and if they don’t improve, you have a clear record of why.

Step 5: Knowing When It’s Time to Let Someone Go

Despite your best efforts, sometimes a team member simply isn’t the right fit. If you’ve provided training, guidance, and a PIP but still see no improvement, it may be time to part ways.

When letting someone go:

Handle it professionally. Be respectful and direct.
Record the meeting (for HR purposes) and follow up with a written confirmation.
Revoke access immediately using an offboarding checklist.

Letting someone go is never easy, but keeping a poor-performing team member only slows down your business growth and creates bottlenecks.

Final Thoughts: Leadership is About Tough Decisions

If there’s one thing I’ve learned in my journey as a business owner, it’s this: Leadership isn’t about avoiding discomfort. It’s about making the tough calls that ultimately move your business forward.

Avoiding these conversations only creates more stress, inefficiency, and frustration. But when you tackle them head-on—with preparation, data, and clarity—you not only strengthen your business, but you also grow as a leader.

So, what’s one hard conversation you’ve been avoiding? Commit to addressing it this week. Your future business (and sanity) will thank you.

Want More Support?

If you’re ready to step into your CEO role, build scalable systems, and lead with confidence, don’t miss our FREE Power to Breakthrough Bootcamp happening from February 17-21. We’ll be diving deep into leadership, team-building, and profitability strategies that will transform the way you run your firm.

Hard conversations don’t have to be scary. They lead to clarity, growth, and stronger teams. The more you lean into them, the more confident you’ll become as a leader.

If you’re ready to take your leadership to the next level and step away from the daily grind, don’t miss The Removable CEO Workshop on February 25th @ 12pm EST. We’ll dive deeper into mindset shifts, systems, and strategies to help you scale your firm without being stuck in the day-to-day.

Join us here!

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