I coach a lot of small business owners, and with women especially, this topic comes up again and again. It’s “How do I not sound mean?” I’m here to tell you, it’s time to call BS on this one.
If you’re an aspiring entrepreneur, business owner, an ambitious, driven person, it’s inevitable, you will have to have difficult conversations.
Conversations about money, letting people go, choosing what’s the best way to move forward for your business. And that last one may mean some career partnerships aren’t going to last. Hey, some personal relationships may not last.
You may start to beat yourself up over figuring out the right thing to say, about when to say it, and if it’s too late to stand your ground. You may be afraid of being labeled as “difficult.” A number of people I’ve consulted struggle with this.
I spent most of my adult life working in advertising as a creative director...yes, like Mad Men. I also co-founded a successful advertising agency and along the way, I’ve had a number of difficult conversations, including letting people go, telling employees they’re not living up to the expectations of their role. Talking to someone about their personal hygiene. About wearing appropriate clothing. Firing a client. Following up on missed payments. Negotiating leases, negotiating raises, negotiating rates and negotiating who takes out the garbage.
I’ve had to have the difficult conversation with my business partner about leaving the business to take care of my health — does that mean a buyout or that we close down the business? And what does that look like? Because I’m married and have a kid, conversations are the bedrock to our way of life. And believe me, as a people pleaser, sometimes these are HARD, difficult things to talk about. Because deep down we all want to be liked. To be admired, to feel like we’re supportive. However, that doesn’t always need to be the case.
I’m going to dive into 5 difficult scenarios you may find yourself in and how to successfully have conversations that meet both your business and personal priorities.
Here’s the top 5 that I work through with people on a regular basis:
Let’s dive in:
We put this one under the category of Disagreements.
If you are someone who has in the past kept your mouth shut but felt silently resentful, this one is for you. If you do not agree with the plan of action that someone or a team has laid out, you can and should speak up.
Business and relationships built on sycophants will only turn out more of the same. Hopefully, by now you’ve seen the data that diversity of thought and approach are what creates innovation and perspective. So how do you feel OK with raising your hand or using your voice? You don’t. It’s going to feel super uncomfortable for a while because it’s a weak little muscle that needs some repetitions to get stronger. It’s like using a 10lb weight at the gym. Eventually, after using that every day for a month, it starts to feel light and you’re ready to move up another 2lbs. So give yourself some slack for fumbling at first and being a little awkward, and give yourself time to do the reps.
Here’s another big part of disagreeing: do not apologize for having another viewpoint. So often we say “I’m sorry, but I disagree” as if the “I’m sorry” makes it more palatable. But it doesn’t. People see through the pleasantries. They also know that behind a “but” is a contradiction.
Own that you don’t disagree. You don’t have to get sassy, just say “I see it another way” or “have you considered it from this POV?” The goal here is to have a discussion. You may never convince the other person to consider your point of view, and that’s OK because now you can decide if that is someone you want to continue having a relationship with into the future.
This one is about Misinterpretation.
When people don’t feel heard, emotions get triggered. It’s a sense of being overpowered and it comes with some knee-jerk reactions. I see it all the time in kids: They want something, it gets misinterpreted, and they blow a gasket. We all want to be heard and to be seen. So recognize today what your triggers are and how to combat them. Right now, grab a pen and paper and write down all the things that drive you crazy. Do you feel frustrated when someone makes a decision on your behalf? Do you get frazzled when someone talks over you? Do you have a hard time expressing how you’re feeling in the moment? Write down this sentence and fill in the blanks:
“When someone does (action), I feel (emotion), because I’ve made it mean (the way it feels).”
What we’re trying to get to is at the end of that reaction. Is it a need to be heard, a need to be right, a need to agree at all costs to feel safe? Now own it. Feel it. Meditate on it. Decide how you can reframe this narrative. This is going to ready you for the next time it comes up. Awareness is what we’re after here. Awareness of our thoughts, and our reactions.
Once you know what went down on your end, pick it back up with that person (or group) and take responsibility for your part in it. Even if someone was screaming at you, you had a roll in that you allowed someone to bully you.
Set some ground rules. No supposing, no accusing or playing the role of counselor. You are there to speak your piece, be understood and come up with ways to avoid it again in the future.
And, please for the love of Pete, do not tell them what they were doing wrong, or how they were making you feel. This is about YOUR part in the way it went down.
The way this sounds is:
“I take responsibility for not speaking up last week. I kept quiet and we missed a big opportunity”
“I take responsibility for not bringing it up to you sooner and letting it slide that you continue to miss deadlines. Let’s discuss how you’re going to get that back on track.”
OR, and this is my favorite one because it’s so true in so many instances:
“I take responsibility for hearing something that wasn’t said. I am ready to listen and discuss.”
If they don’t respond with anything, then they have some growing to do and you politely leave the conversation thanking them for the chance to clear the air. This is key. Don’t labor it. No dwelling or calling them silent names. If you’ve taken true responsibility for your part, you will feel empowered and a sense of relief. Most times this usually gets the other party wanting to take some responsibility and discuss further and then, voila! You’re on your way to better communication.
Some great work by Brene Brown with her Dare to Lead is a good way to get under this one.
This is about Expectations and clarity of roles.
Whooo boy. You’ve put time, energy and love into someone to work with you or for you and you find they’re not holding up their end of the workload. This means you lead the conversation about expectations and roles and responsibilities. What you were expecting should be documented and agreed upon at the beginning of the relationship. The next part of this is nipping things in the bud early if you see a pattern developing. Do not wait for this to get better with cues of long sighs and passive-aggressive statements.
If once you’ve either set the record straight with expectations or reminded them of what they agreed to in the beginning, don’t let it go too long without another check-in. Set a metric for success and a “by-when” date. (by when can I expect this to be complete?) Most people will want to do right by the situation and correct it quickly.
If they cannot hold up their end of the bargain a second time, then ask them without any more fluff than this: “How can I keep this relationship going and count on you after you’ve missed this a second time around?” How we do one thing is how we do everything. So if they blow off that second chance, they’re most likely going to do the same for additional chances. Do yourself the favor and decide early if you’re going to let someone go and do it then because the longer the problem persists, is a dent to your health, happiness and bottom line. It’s also toxic for the workplace as people can pick up on that energy, or even worse, start to replicate the habits because they see it’s tolerated and commonplace.
My favorite resource for this is a book by CIA hostage negotiator Chris Voss called “Never Split the Difference” and is a great resource for gaining listening and negotiating skills.
Buckle up, buttercup, this one is about Self-Worth and Value.
Most people, well most Americans, have issues with money. It doesn’t grow on trees, you have to work hard for money, it’s only for rich people, and rich people are gross and self-absorbed. We find subtle subconscious ways to counter being a self-aggrandizing affluent narcissist, and we (inadvertently) give all our money away or sabotage our chances of making big money.
Before you ask anyone for any money, first go on a little exploration of where your money conversations are REALLY at. You may think you want money, but then tiny little actions help you from reaching your goals. Case in point: Asking for help. Asking for money. Billing people for what you’re worth. Following up on that unpaid invoice. Letting people slip with paying you back.
Make it easy on yourself. Don’t guess at what you’re worth. Create a formula, put it in a spreadsheet and use this as your baseline. Here’s the formula:
That’s your base cost. If you’re offering something of significant value that will change someone’s life or the course of their business, you can charge a premium for that, it’s called value. Set a price for this, again. Do. Not. Guess. Stand by your pricing. You’ll undervalue yourself every time if you do not.
My favorite resource here is Jen Sincero’s You Are a Bad Ass at Making Money. (No joke, I’ve read this 4 times and listened to the audiobook at least 9. LIFE CHANGING.)
Well, hello Boundaries, nice to finally meet you!
This is the biggest one for me recently. I genuinely want to help everyone I meet. And I can help them in so many ways. It also comes easy to me, so why not? But what I have come to realize that is if I don’t help me first, I can’t help anyone. The way this looks is creating a YES and NO list in accordance with your goals. What goes on this list is everything that will push you closer to your goals and those things that don’t.
You can revisit this as you get a little further along of course. But it’s essential to start saying no to people. Are they going to hurt and upset? Perhaps. Especially if they are used to getting things from you and suddenly there are boundaries. Be clear on what you can and cannot do. Be patient with people as you help them understand that your time is the most valuable resource and you need to do you for a while. Mostly be patient with yourself because this isn’t a perfect process. You may slip back into old patterns, or feel obligated to soften. Recognize where your trigger was for making an exception to your YES and NO list, and make a mental note on strengthening that for next time.
To recap: You’re not being mean. You’re being honest.
And when you can claim your own honesty and truth and communicate that clearly, that’s the winning combo. Don’t think you have to have it perfect, or understand how to get to the end of it, just start practicing in small ways, every day and soon it will be second nature.
Still need more guidance? Sometimes we need a coach to work with us until we find our footing. I offer individual and group coaching through the tough and unknown. Drop a note and say hello.
Join our mailing list to receive the latest news and updates from our team.
Don't worry, your information will not be shared.