#3 | Stop Confusing Discernment With Decision Making

Not every decision carries the same weight, and not every moment requires the same kind of clarity. In this episode, Dr. Daniel Freeman draws an important distinction between discernment and decision making. One is about learning to see clearly beneath the noise.

The other is about choosing a path and moving. Leaders often rush to decisions before they have developed discernment, and that is where costly mistakes begin. This conversation offers a more thoughtful framework for knowing what season you are in and what the moment actually requires.

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Available for Speaking I'm selectively available for keynotes, leadership retreats, and executive panels on decision-making, organizational culture, and leadership identity. If you're building a lineup for your next event, I'd love to be in that conversation. 

→ Reach out at dan@fsgventures.biz or  YourExecutiveThoughtPartner.com

If you made it this far, I want to offer you two limited time discounts. 

• Executive Thought Partner 3-Month Commitment
• 8-Week Fundraising Intensive Program 

View this form to see the discounts:https://forms.gle/ngxwgS6sjCpyppuA8

Transcript

SPEAKER_00 0:02

Welcome to the Executive Thought Partner Podcast, where leadership, strategy, and growth intersect. I'm Dr. Daniel Freeman, Executive Thought Partner and co-founder of the Growth Alliance. This isn't just a podcast about fundraising. It's about how leaders think, decide, and build systems that scale impact across nonprofits, higher education, athletics, and mission-driven enterprises. Here we explore major gifts, governance, culture, and the quiet decisions that determine long-term momentum. If you're leading something that matters and you want clarity with conviction, you're in the right place. So when I start these recordings, I want to think to myself, what's the point of it? What am I trying to bring to you, the listener, through these podcasts? And I think what I really want to bring to you is information and knowledge through which I see the world, the lens in which I see it through. And today I want to talk about discernment from decision making. Now, if you're a leader, I hope you know what discernment is. If you're not a leader, discernment is essentially the awareness of yourself, and what comes from that is the decision-making ability, in simplest terms, on whether your knowledge, what you have to say, or what you see is valuable to the conversation and the scenario that you are a part of. It's always good to give an example of what discernment is not. And discernment is not being in a meeting, someone saying something, and you feeling like you have to cut them off, or you have to push back on what they say, especially when that should be a separate conversation from the larger discussion that's going on. That is not using good discernment. So, what I want to talk about is how do you use discernment? What does that mean? What kind of scenarios have I been in? Because discernment is really spread out, right? Discernment isn't just I'm in a meeting, maybe I'm entry, maybe I'm middle level, maybe I'm a leader. And should I say something or should I not? Will it add value to the conversation? Will it push the conversation forward and to go back? Not just will it add value to the conversation, will it add value to the person who began the conversation looking for general information? And if the answer is no, then you should not speak, because that's going to turn the discussion, which could be concise, intentional, and direct, into lots of miniature conversations that should be held outside. So that's understanding discernment, but discernment can go into everything. It's not just those meetings. We can talk about donors, we can talk about one-on-one meetings, we can talk about colleague meetings, we can talk about what undermining looks like and the connection to discernment related to that. But I think let's just talk about the first piece and let's let's talk about it from a fundraising and operational and general perspective. So you're in a meeting, let's say you're entry level and you were brought into that meeting because leadership saw that you had promise, or you're middle management, right? You're a director. But you were brought in because your expertise and your team is working on problem scenario issue that's going on in your organization. The president speaking, chief of staff speaks. You're thinking about everything that they're saying, which is good. You should be absorbing everything that they're saying in that conversation. You shouldn't be thinking, what's the next question I should ask? You should be thinking, what is the next answer they're going to give me? And how hard can I listen? And how hard can I process that answer and really put that together to then inform anything that you say at that table. So they're talking, they're talking, and you hear it. You hear that moment where you think to yourself, I have to jump in. This is it. This is me. I want you to pause for a second. I want you to take a mental step back. And I want you to first ask, have I been processing everything they've saying? Everything they've been saying, is everything that they've been sharing and speaking about in the conversation, if I add in my two cents, is that going to move their conversation forward? My team oversees it. Your job as, even if you're a middle manager or director, your job as the leader of your team is to remove any speed bumps or any blocks that slow down acceleration and make the job of your direct reports harder. That is your job. You are the buffer between leadership and you. So I ask you again, in that conversation, if you speak up at that moment, will your words benefit your team? Will it expose them to some undiscovered issues or some undiscovered anxieties from leadership that's going to bring more questions? And then you're going to dig yourself a hole? Or is the piece of information or knowledge that you're thinking about in that conversation at that moment, could that be held for a one-on-one meeting that you'd like to have with your supervisor, the president, leader, whoever it is that you report to, could that wait? Because that's the superpower there. There are a lot of people who sometimes it looks like they play the game when they decide not to speak or take part or do different things in meetings. But there's an alternate way to look at that, because you know my take on playing the game. I've talked about that. But what's more important is because you are leading and looking out for your team, if it's better for you to advocate for them and the work that you're doing together in a small group fashion where you can explain yourself and go into detail versus trying to explain yourself in a large meeting when you're not going to get the time that you need. I think that we know the answer. And that answer is to take a pause, take your notes, and then be able to have a side conversation with your supervisor later where you can extrapolate on everything that you're thinking about. Because that's what those meetings are for. Now, we talked about that side of it, right? There's another side of it. One-on-one conversations. Could be you and a direct report, could be you and a supervisor, could be you and the CEO of your organization. Now we talked about discernment. Take a second. I want you to say, what is discernment allowed? When you say what is discernment allowed, I want you to think out loud that discernment is just awareness. It's the awareness that you have and the power you have with your words and what you choose to do with them. So you're having a one-on-one meeting. We'll call it with your supervisor. And maybe we'll look at a scenario with your direct report as well. But let's start with your supervisor. You're in that scenario, you're having a conversation, and you can tell and you can feel the vibe from your supervisor, you can feel the energy. They're feeling a little bit anxious. They're asking you questions, you're sharing the data, you're showing them the graphs, you're showing them money raised, money coming in, what things look like. And it just doesn't seem to be enough for that supervisor. And they're grilling you, but you're calm, you're collected. You're not giving too much information to dig yourself a hole. You're not giving them information that's going to spur them to ask a million different questions about things they don't know about that you're the expert for. But then you're going to have to explain yourself. And the moment you explain yourself, they're going to try to catch you in something. Doesn't work out that way. That's not good. What I want you to do is I want you to take a breath, just like you did when you were invited to that executive team meeting where the CEO and your supervisor and others were speaking. And I want you to ask yourself, have I really been listening to everything that my supervisor is saying? Or have I been listening to their question and then just answering it? Because the best thing that you can do with discernment is not just continue to try to answer questions. The best thing that you can do with discernment is actually ask questions yourself. So I want you to think about that. If you are leading a nonprofit, college, foundation, athletic program, or mission-driven enterprise, and the weight of key decisions sits squarely on your shoulders, this is for you. I'm Dr. Daniel Freeman. Through my executive thought partner practice, I work alongside founders, presidents, CEOs, and advancement leaders to refine strategy, strengthen major gift growth, and bring clarity to high-stakes decisions. And through the Growth Alliance, we help organizations build the systems and structure that turn vision into measurable momentum. This isn't surface level consulting, it's focused partnership for leaders ready to scale impact with intention. Visit fundraisewithdan.com to start the conversation. I want you to ask a question. And the question you need to ask is what do you really need for me? This whole conversation, your supervisor has been asking you all of these questions to try to figure out the answer because they don't even know what the answer is. They don't know what the real question is. So I want you, when you take that step back, I want you to look at your supervisor and say, it sounds like you're very curious about XYZ. And I want to provide that answer for you. But I'm slightly unsure of what question you really need to ask to get the answer you're looking for. And I want to help save you time and figure out what answer I can give you directly that will give you everything that you're looking for. Now you have to do that tactfully because you don't want to come across as bigger than your supervisor. But you also want to come across as I'm listening so intently to you in this conversation that I want to give you exactly what you're looking for because I know that if I can give you exactly what you're looking for, this all stops. And their level of anxiety, it drops. But we're so used to continually just trying to answer the questions versus taking a step back and asking one or two questions ourselves to help target what exactly is the information they're looking for. Now let's talk about your direct report. You're in a scenario, your direct report comes to you, and you feel like they've been off a little bit. And you start asking them questions. Okay, what did you work on last week? What was your production? How many proposals did you put in? How many sales calls did you make? How many general calls did you make? What did your contacts look like? Did you put them into the system? Did you close any deals? What kind of collaboration opportunities are there across the organization? And they're giving you the answers, and you just keep asking questions, but you don't know the answer you're looking for because you don't know the right question to ask. And that's where discernment comes again in a different way. Take a step back and just sit in silence, sit in your silence for a minute and let your employees sit there as well. And be transparent with them. Let them know that you're trying to ask a question that you can't necessarily figure out because that vulnerability is going to show them that you care about asking the right question, not just questions to question them. So instead of continuing to ask them questions, you could ask them related to, say, this scenario, what do you feel great about that you accomplished last week or this week? And tell me how you feel that will push our mission and our goals forward. Because what you've done is you've now given the power and the discernment to your employee. You've now asked your employee, how are you making a contribution that is going to move the organization forward? And their answer is most likely going to give you insight about where their direction is. Because that's what you're trying to do. You're trying to figure out where are they looking? What are they focusing on? What are they taking action on? And once you do that, you can understand where they are, and then you can say, Oh, okay, I understand that. What I'm looking for you to do in a way to move the organization forward is X. Right now, you're looking at Y. And I think that's where the miscommunication comes from. Now, the last thing I want to talk about is undermining. We're going to call this a level, one-on-one conversation with a colleague. Have you ever sat in a conversation with a colleague, shooting the talk about the organization, gossiping, had a general conversation where you talked about what's going on, what you're both working on, what that looks like, about your goals, what you've raised, what you've accomplished for the year, bonuses, the way the organization's moving, donors, prospects, whatever it may be. Maybe you've had that conversation where you have to think about what I can divulge? Can I say everything that's on my mind? Can I trust this person with this information? Maybe. Maybe not. I hear from leaders all the time. When they tell me things, they pause and they say, I'm not sure why I'm telling you this. And then I tell them, no, no, no, keep going. Like it's fine. This is between us. They talk a little more and they pause, and I ask them, Don't you talk about this with anyone else? And the thing that I always hear is, Well, I can't tell my number two. I can't tell my chief of staff. Because what if they tell the rest of the team? What if it leaks and the rest of the team starts to drop on their production? Or they start to question my direction, which I'm already questioning myself because I'm a leader and I'm always trying to look ahead of what's next. What about colleagues at other places? Well, I can't talk to them. They're my competitor. You know, they may not be in the exact same business, but the relative work that we're doing may be in the same sector. Or maybe it's not that. Maybe it's the fact that if what if they tell someone over there, tell their friend, CEO in another company? What if that company decides to use that against them? What if that company CEO knows people at your organization and they tell them what you had told them? And then that starts to get passed around. And people are like, why are they talking to our competitor? Why didn't you know they tell us this? Where's the transparency? Where's the communication? I can really backfire on you. So that's what I'm talking about when I am suggesting. You need to think about what you can divulge. That's why I have my work as the executive thought partner. I sit in the trenches and I partner with executives and leaders to pressure test decisions, to talk about pressures, to talk about internal politics, to talk about not strategies, but how they feel about strategies, why they're choosing strategies, the motivation behind strategies of hiring and sales and marketing, whatever it may be. Not the insides of it, but the decision making that determines why they're doing those things. And it provides intellectually stimulating conversations for them. Something that when someone asked me that question, I realized, you know what? I wasn't having intellectually stimulating conversations with people internally. It was always people external of my work, donors, peers at other institutions, other leaders. Those were the best kinds of conversations that I had and I provided. And that's why I want to provide the executive thought partner. So again, I want you to think when you're in this conversation with your colleague, what can you say? What's going on? Who's noticing what? So that when you have that conversation, they can't come to you and say, Oh, you want to do that? I don't see you as a leader. You need to work on your internal relationships. You need to work on your network. I don't think you're in a position for any of that. That's something that I've heard directly. And that's stung. That definitely stung. But you know what that means when you're in that conversation? When someone says that to you, they think that they're trying to put you down a notch. Maybe because they're self-preserving, maybe because they feel threatened. But by them doing that, they're divulging so much more information. They think that they're putting you in your place. But when someone says something like that to you as a colleague, they're divulging so much more than they should. They're showing you what they really feel on the inside about you and about your work. It's not a reflection of you and what you are accomplishing, it's a reflection of them and the lens in which they see you. And that's not someone that you need to spend time with. So when I talk about one-on-one discernment, especially with colleagues, when someone says something like that to you, I want you to pause. And there's a there's a former attorney on LinkedIn, TikTok that I listened to, Jefferson, and and he always says, ask them to repeat it. When someone says something to you that throws you off a little bit, look back at them and tell them, I'm sorry. I don't really, I don't know if I heard you correctly. Can you repeat that for me just to make sure that I heard it? That's discernment. Discernment is your awareness of everything around you and the way that you fit into those situations and conversations. And when you ask a question like that and you ask someone else to reflect on what they said because you're more aware of the situation of yourself and of them than they are of themselves, that's when you level up. That's what I want you to think about today. Think about how aware you can be of yourself, your situation, and of others. And instead of putting others down, you can ask people to reflect on what they've said and what they're thinking and all these different conversations. That's what it means to be a leader. That's how you be direct without putting others down. So this is executive. Thought Partner number three. If you want to see more about what I do, you can go to Fsgventures.biz to see more about the Executive Thought Partner, the work that I do. And comment and like on this podcast episode. Let me know what you think, and I'll see you next time. Thank you for listening to the Executive Thought Partner Podcast. If today's conversation helped clarify your leadership or expand your thinking, share it with someone navigating meaningful decisions. Through my Executive Thought Partner Practice and the Growth Alliance, we work with leaders and organizations ready to strengthen strategy, align systems, and build sustainable momentum. You can learn more at fundraisetdan.com. Until next time, think clearly, lead intentionally, and build what