3 Tips to Turn Tough Conversations Into Profitable Ones

How might we learn how to say no?
3 Tips to Turn Tough Conversations Into Profitable Ones
Image credit: sorbetto | Getty Images

Franchise Your Business

Schedule a FREE one-on-one session with one of our Franchise Advisors today and we’ll help you start building your franchise organization.
Entrepreneur Leadership Network Writer
Award-winning Speaker. Author. Coach. Master Communicator.
5 min read
Opinions expressed by Entrepreneur contributors are their own.

As an entrepreneur, your life immediately becomes easier the moment you realize it's happening one conversation at a time. As soon as this concept fully takes root in your DNA, you instantly get that the quality of your life -- and your business, your relationships, etc. -- is a direct reflection of the quality of your conversations.

The majority of these conversations come and go, but on average, every single entrepreneur engages in six to nine significantly meaningful conversations per day that will influence their future. Sales, marketing, hiring, customer service, innovation and mindset are topics filled with tough conversations. When these tough conversations are navigated successfully, they become highly profitable conversations and yield the results you desire.

Related: Why Mastering the Art of Conversation Will Make You More Money

If you want to triple your profitability this year, start with turning your tough conversations into your most profitable ones with three proven tips.

1. Every tough conversation should be framed as a “How might we…?” question.

Whether you want to increase sales 12 percent, grow the team, increase efficiencies or start a new online ad campaign, phrase your goal or objective as a “How might we…” question and you’ll get your peeps aligned around problem-solving.


  • How might we increase sales 12 percent?
  • How might we attract and retain top talent?
  • How might we create a campaign that truly engages our prospects?
  • How might we resolve this to create a win-win for everyone?

These three magical words open up possibility and increase engagement and buy-in from your team members, your business partners and your customers. At your next meeting, start with an overarching “How might we…” question, and you’ll witness a robust dialogue that will drive your business forward faster.

2. Make space for possibilities with offers and requests.

You need to ensure action. The whole point of a tough conversation is to create a profitable result. Profitability can be measured as time, dollars, energy, connection, breakthroughs, relationships started or ended, problems-solved or boundaries established. There’s a myriad of ways to generate and define profitability, but we must ensure action to create the future we desire.

These actions might include:

  • Offering grace to yourself when something doesn’t go as planned.
  • Requesting an apology when necessary.
  • Offering an idea.
  • Requesting a new behavior. 
  • Offering resources or support.
  • Requesting a new deadline, terms or agreement.

At the end of every conversation, to make certain it’s profitable, you must make an offer or a request. Words without action will not get you where you want to go or get you what you want.

Related: 5 Ways to Build Courage and Competence for Difficult Conversations

3. Know your lines, both what to say and where to draw ‘em.

Golden lines spoken and golden boundaries drawn can turn a super hard conversation into a veritable pot of gold. Proven one liners can be magically helpful and needed. And when you got ‘em in your back pocket, you are far more confident and competent in successfully handling tough moments.

Maybe you’re dealing with a difficult person who’s back in your office complaining again. Instead of giving him or her more of your precious time to vent, you ask, “How are you hoping I respond to this?” or “What action are you hoping I take?”

Instead of taking the complaint and accepting responsibility, you put the responsibility of thinking back on the difficult person. You stop the whining and shift the conversation to better understand their desires and outcomes. What do they really want?

Or maybe someone says something egregious in a meeting. Super snarky. Definitely not helpful. Instead of escalating the situation, you invite them to your office and ask, “What was the thought behind that remark?”  You’re now leaning in instead of reaming out.

In addition to having a few good lines to say, know how to draw a few good lines in the sand. I’m talking about boundaries.Tough conversations only get easier when you have a strong sense of self and self-worth, meaning you have clarity on where another person ends and your sense of self begins.

A lack of boundaries is self-sabotage, so let’s start with a basic one -- no thank you. All you people pleasers, all you go-along to-get-alongers -- saying no can be difficult. Yet, when you get clear on what you’re actually saying yes to, it gets a whole lot easier. Saying no does not require an explanation nor does it require an apology. But it does require clarity. What are you saying yes to?

Imagine the next time someone says, “Can you do this for free? It’ll be great exposure for you.” Instead of acquiescing and saying yes, imagine yourself confidently saying, “No thank you,” or saying, “In order to share my services I’ll need X in return.” If you really aren’t interested in having your services or products exploited, stop and ask yourself, if I don’t want to volunteer my time or product for free, what am I saying yes to? More time with my family? Self-respect? Integrity? Investing my time in a better opportunity? Ensuring my value?

Related: Why Saying 'No' is the New 'Yes' for Entrepreneurs

Once you get clear on the yes behind the no, it’s much easier to say it. Getting clarity on what you’re saying yes to is an awesome technique for increasing your confidence and saying no with conviction.

Every entrepreneur who navigates tough conversations successfully gets one step closer to living the profitable life they desire. Isn’t it time you lived your most profitable life?

More from Entrepreneur
Our Franchise Advisors are here to help you throughout the entire process of building your franchise organization!
  1. Schedule a FREE one-on-one session with a Franchise Advisor
  2. Choose one of our programs that matches your needs, budget, and timeline
  3. Launch your new franchise organization
Discover the franchise that’s right for you by answering some quick questions about
  • Which industry you’re interested in
  • Why you want to buy a franchise
  • What your financial needs are
  • Where you’re located
  • And more
Make sure you’re covered for physical injuries or property damage at work by
  • Providing us with basic information about your business
  • Verifying details about your business with one of our specialists
  • Speaking with an agent who is specifically suited to insure your business

Latest on Entrepreneur