Tuesday’s Tips — How to Tackle That Difficult Conversation
28 Jan 2026 · 7 min
Podcast episode (hosted by Bill Gallagher) offering coaching on preparing for difficult conversations using role‑play techniques. Uses an anecdote about a client named Alex to illustrate multi‑mode role‑play (playing worst‑case, clean ‘no’, reversed roles, and expecting ‘yes’) to reduce fear and improve outcomes; includes sponsor/promotional reads for Doxatalent and Align/Scoreboard (Scoreboard by Align).
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Hey everybody, my name is Bill Gallagher, scaling coach and host of the weekly Scaling Up Business podcast. We do a couple shows a week on everything to do with the world of scaling up. Your people, your strategy, your execution, your cash, how to get it all right, how to grow and develop your business and how to develop as a leader in the process that leads that business. So anyway, back to the example. So I'm working with this guy some years ago, his name is Alex. And Alex had a conversation, a difficult conversation to have with the board. So he went to his board to have a conversation about a budgetary issue that was really, really, he was expecting it to go very badly and he'd been putting it off for a few weeks. So what we did, I think makes a huge difference in difficult conversations. We did some very specific kinds of role plays with it. I've used this again and again myself and with other coaching clients. And it's so powerful. You don't need a coach necessarily to do it. You could do it with a friend, a buddy, a co worker, any number of different people. So we role played the conversation a couple of different ways. First of all, we role played the conversation. I represented a particular board member and Alex had the conversation with me and I played that board member part in the way that he was really worried it was going to go. So I was the person and I did the, the, you know, the, the best example of what he was most worried about. And we did It a few times until he got really comfortable with it so that it could go badly and he could still be talking, right? Still keep the conversation alive, even if it was going as horribly as he thought it might go. Then we role played the same conversation and I just said no. And he kept finding different ways to ask and create and keep the conversation alive while I kept saying no, no, no, no, no, no, no. So first is the. So all the other connotations around it. And then there's simply just a clean no. And he's getting. All the while in this, Alex is getting more and more like loose and easy and that kind of thing. We played with driving the emotion up and down in the whole conversation until he just was loose. Like we'd done the practice preparation. Then we did a couple times where I reversed it and I played him and he played the board and he got to see how somebody a little more flexible, not like rooted in his skin and his DNA and all that, his pattern, his history might do it, which opened and expanded his mind. And then we did one more time where we roleplayed the conversation and he just went in expecting it to go well now, having done all the others. And I didn't make it too easy for him, but I just didn't resist either. I bought into his logic, I played along with him and I said yes. The interesting thing in this last one is that he was really ready, been through all the other spaces of it and his logic, his arguments, it all made much more sense by this point because he was expecting yes, he was speaking and in sync with all of that. You could also add a role play where you are playing with and listening for what that other person cares about. So there's a variety of ways you could role play, but the fundamental practice here is role play play with the fear. Work through it until you're comfortable in the face of the fear. You haven't overcome it, but you have courage to move through it. Play with the no that you're worried about getting. Play with the whole range of it. Even try it reverse roles so that you see how somebody else might play with the same thing that you're all wrapped up about. And then finally go in there and do a version where you're expecting yes and see how that feels and see how free you feel. Anyway, the long story short is Alex went and had the conversation the day or two later and he got everything he wanted and then more. And they're like, oh, it's so great you brought this up. Now there were objections and concerns and things like that. There was a conversation. It wasn't an easy slam dunk, but he'd gotten himself so worked up in his own mind and had he not done the preparation, he could have been triggered and then just gone, you know, in some other weird direction and not had a very productive. But he was completely loose and free and he did a fantastic job, got everything he needed and wanted and that led to a great next period for Alex and for the company. So I hope that's helpful. Thanks so much. Keep scaling up, Keep tuning in like subscribe, come on back. We bring new things to you every week. Are you ready to turn your goals into daily wins? You should check out our Scoreboard software. Powered by Align, it's the official software for scaling up. With Scoreboard, you'll get an AI driven coach for priorities and KPIs and it'll help keep your team focused on what matters most. With Align, you can track your goals in real time and you'll even see results on the go. With their mobile app, you can rest easy knowing that Align has world class onboarding and support to set your team up for success. This is really more than just software, it's what I actually use to manage growth in our scaling up client teams. Unlock clarity and results with Scoreboard by Align. To try it now, go to aligntoday.com Bill G One more time. Aligntoday.com Bill G that's aligntoday.com Bill G Check it out and try it now.




