The 8 Most Uncomfortable Conversations You’ll Have as an Entrepreneur

By Katlin Smith


Launching a business and taking a product or service to market is courageous.

It doesn’t mean the uncomfortable discussions you’ll have as an entrepreneur will be easy.

In fact, challenging dialog with employees, investors, partners and others at your company is something you’ll never really get comfortable with. You’ll learn to master some things, you’ll learn to avoid others.

If you think you’ll always be able to default to your leadership and management layers, think again. Plenty of the conversations that you don’t want to have will take place with you at the forefront.

Being at a high-growth, funded business, I’ve had a fair share of them. The good news is, tough talks often lead to new beginnings, better growth, and far more positive outcomes than not.

Here are the difficult conversations you’ll likely endure at your company – and how to ace them:

“That was inappropriate.”

Addressing inappropriateness can be sticky to navigate. There are things that can and can’t be said and done, or you may risk a lawsuit. Be sure you’ve checked into any legality before you discuss it. Subjugate emotions and feelings, keep to the facts, and clearly define what is appropriate so it’s clear next time.

“We/You/I failed.”

Everybody makes mistakes, and everybody misses the mark sometimes. Even with the best planning and effort – and it can include your own failure. Identify what went wrong, learn from it, and quickly move to the solution you have in mind. Failure is inevitable – put the focus on how you can recover from it.


Teams, partners, vendors, and investors will constantly ask permission – to take time off, to make a move, to incorporate ideas. Get acclimated with saying no because you’ll do it often. At Simple Mills, I keep open to asks across the organization – and if the answer is no, I share why. Most of the time there’s a good reason you’ve declined a request. It can help others to understand when you give context.

“You’re fired.”

Letting go of employees, vendors, partners, suppliers – the list can be endless at any company. It can be due to performance, or it might be that you need to cut back somewhere. Hit these discussions early on. Don’t wait until the end of the day/call/week, etc. Be direct, honest and keep it simple. Allow for questions and dialogue.

“You’re not getting the promotion/bonus/position.”

This talk is usually harder when you’re holding it with an employee, or someone who has a relationship with you or your company. You may face disappointment, anger, or upset. It can be easy to shrink back or overly apologize. Control your fears or feelings, lay out the facts, and be prepared in advance for how you’ll handle any reaction.

“We’re cutting back.”

Budget cutbacks and changes are not uncommon in business. But trimming costs or cutting spending can be terrifying for employees, partners, and others in your organization. You don’t need to breach these conversations with immense detail or reasoning. Simply articulate what you have planned, and what it means for various parties involved. Be prepared to answer questions and address concerns.

“We’re making a leadership/management/department change.”

Change happens, particularly in the first few years of your business. It can mean discomfort, shifting priorities. It may require new processes and protocols, or different roles and job duties. Involve people where and when it makes sense – your senior leadership team may get first notice, before a formal plan is in place. Alert others in your company as you’re ready – but before the changes are made.

“I’m sorry.”

Admitting you’re wrong can feel – and leave you – vulnerable. You might fear losing your position of authority and leadership, or that you’re enabling employees, investors, etc. to pile up against you. On the contrary, it can demonstrate solid leadership to know when you should apologize – and do it. Admit you’re wrong, move on.

Workplace Issues

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