Drafting Our Strategic Dream Teams

There's a push right now to democratize strategic planning, where organizations survey the community, poll the staff, and put the big calls to a vote, sometimes right down to the budget. The instinct behind it makes sense, but it goes too far.

Your community should have a lot of influence on your strategy. That still doesn't mean putting your strategy out to a vote. Influence and decision-making power are two different things, and when leaders treat them as the same thing, good orgs freeze.

It plays out in a familiar way. An ED gets so worried about how the community or the staff will react that they can't make a choice at all, and the whole org stalls waiting for a consensus that isn't coming.

All the inputs matter. The leadership team, the community, the data, the gut, a trusted outside voice, peers, the board, the funders. You gather all of it, you look for patterns, and then at some point you stop gathering and you decide, knowing you'll never have perfect information.

If everyone walks away from that decision happy, the choice was probably too safe. The real wins are the ones where someone disagrees with the path you took and still can't argue with the results.

Put to a board, it comes down to this: synthesizing all of it into a call only leadership can make, and then owning it, is the actual job. A plan you never execute is worth nothing. The only one that counts is the one you actually run.
 

Episode Highlights:

[00:00:00] The premise: drafting fantasy strategic planning teams from ten possible inputs
[00:02:00] The ground rules and why every input is assumed to be trusted 
[00:02:30] First picks: leadership team vs. the community you serve 
[00:05:15] Influence vs. decision-making power, the distinction that runs through everything 
[00:07:00] Why fully democratized strategic planning goes too far 
[00:08:45] Gut and intuition as a legitimate strategic input 
[00:10:45] Data beats opinions, and the difference between predictive and directional data 
[00:13:45] The case for a trusted outside consultant or strategist 
[00:15:45] Drafting the board, and why boards should support more than they decide 
[00:20:15] Peer organizations as input and potential collaborators 
[00:22:30] Major funders as another audience you have to serve 
[00:25:30] Where frontline staff and public feedback land, and why 
[00:28:30] How to actually synthesize all these inputs into a decision 
[00:33:00] Win-win as a cheat code, and why pleasing everyone signals a weak choice 
[00:31:30] Minimum viable strategy: the only plan that matters is the one you execute

Notable Quotes:

[00:05:35]: "The community should have a lot of influence, but I don't think this work usually works when it's truly democratic." Eric Ressler 

[00:11:05]: "We have a saying at Seymour Center here where data beats opinions 100% of the time." Jonathan Hicken 

[00:09:30]: "Sometimes gut level decisions get not as much credit as they should, because the body and the brain are actually really tuned to making complicated choices by intuition at a pretty good rate if you have the right inputs in your daily life." Eric Ressler 

[00:34:30]: "It's not about finding emotional harmony. It's a cheat code almost that's going to unlock everybody's success." Jonathan Hicken

[00:33:35]: "If literally everyone is happy, maybe the decision was too obvious and weak and there should have been a little bit more of a bold choice made." Eric Ressler 

[00:32:10]: "You could plan forever, but the only plan that really matters is the one that you actually execute on." Eric Ressler 

Resources & Links:

• Designing Tomorrow Spotlight interview with Rob Acton on designing effective nonprofit boards
• Cause Strategy Partners — Rob Acton's firm, focused on nonprofit board placement and governance training

P.S. — Struggling to align your message with your mission? We help social impact leaders like you build trust-building brands through authentic storytelling, thoughtful design, and digital strategy that works. Let's talk about your goals »

Full Transcript:

Jonathan Hicken [00:00:00]: All right, Eric. Here's what we're doing today. We are going to draft fantasy sports style draft of our ideal strategic planning teams. This comes from some questions that I often get from people in the community and funders and stuff, which is like, Jonathan, how did you come up with this strategy to be a collaborative center for coastal resilience? Where did that come from? And I've actually found that a pretty challenging question to answer because I really did collect a lot of input from a lot of different parties here. And so I thought it might be fun today to actually assemble our ideal teams of influencers when we come up with our strategy.

Eric Ressler [00:00:55]: Okay. Super excited for this. Building a little bit off of the energy of our tier ranking brand strategy video. So we have 10 that we've pre-selected, right? We're assembling our teams. We get to pick one at a time. I guess it's your episode so you get to go first? How's this work?

Jonathan Hicken [00:01:15]: Yeah. Couple of ground rules before we get right in. So we've listed 10 potential inputs and I'm going to read them randomly so I don't tip you off into my order here, but here are the 10 real quick. So a trusted consultant, frontline staff, your gut intuition as the ED or CEO, data, the community you serve, your leadership team, major funders and donors, your board, peer organizations, and frontline staff.

Eric Ressler [00:01:45]: I mean, just hearing this list makes me feel for EDs. I have to make these choices and it's going to, I think, create a little bit more empathy when I get frustrated with clients where I'm like, "Could you just make a choice already?"

Jonathan Hicken [00:02:00]: Yeah, there's a lot of people we got to listen to. There's a lot of people.

Eric Ressler [00:02:00]: Okay. I'm excited. Let's go.

Jonathan Hicken [00:02:00]: So ground rules. First of all, we have to assume for the purposes of this conversation that all of these different parties are trusted people, right?

Eric Ressler [00:02:10]: Good inputs.

Jonathan Hicken [00:02:10]: Good inputs, good relationships, et cetera. So obviously there's going to be variation in reality. It's a big leap.

Eric Ressler [00:02:15]: A big leap, but I'll go with it.

Jonathan Hicken [00:02:15]: That's going to just be an assumption. And so we're each going to be creating a team of five. So I will give you the honor of making the first pick. And then I will go and then we'll go back and forth until we've selected all 10. And then if I've picked one, you can't pick it. Off the board.

Eric Ressler [00:02:35]: And then we're going to have our teams fight at the end or...

Jonathan Hicken [00:02:40]: Come up with the best strategic plan. Yeah.

Eric Ressler [00:02:40]: Okay.

Jonathan Hicken [00:02:45]: All right. So let's get right into it.

Eric Ressler [00:02:45]: All right. So my first pick is leadership team.

Jonathan Hicken [00:02:50]: Ooh, okay. All right.

Eric Ressler [00:02:50]: Was that yours?

Jonathan Hicken [00:02:50]: It was not. I'm not going to tip that off though.

Eric Ressler [00:02:55]: Okay. So my first pick is leadership team and that is because if I only had one team to assemble to make strategic choices, it would be that team. And I think that's because if your team can't be that team...

Jonathan Hicken [00:03:10]: You have the wrong team.

Eric Ressler [00:03:10]: You have the wrong team. And maybe you do have the wrong team and maybe you know that and so that shouldn't be your first pick. But we're working off this assumption that all these inputs are kind of where they should be. So in my opinion, at the end of the day, in terms of who actually influences and makes decisions around strategy, it better be your leadership team.

Jonathan Hicken [00:03:25]: So in that, I sort of have some assumptions here, right? That having the right leadership team means they deeply understand your community, they deeply understand the business, they deeply understand operations, funding, budget, et cetera, et cetera, et cetera.

Eric Ressler [00:03:45]: They've already probably been influenced by the other nine in their lived experience day in and day out, potentially for years. This gets a little complicated for that reason, but leadership team is my number one.

Jonathan Hicken [00:03:50]: Solid pick right off the top. My first pick is going to be the community you serve.

Eric Ressler [00:03:55]: Ah.

Jonathan Hicken [00:04:00]: Yeah. That was your number two, wasn't it?

Eric Ressler [00:04:00]: My number two. Yeah. My top three if you hadn't taken them would have been solid, but okay. I'll work with it.

Jonathan Hicken [00:04:05]: Yeah. There has to be some signal from the community you serve. If you're doing a strategic planning thing, that probably means that there's something needs to change.

Eric Ressler [00:04:15]: Or it's just three years are up so it's time for a new strategic plan.

Jonathan Hicken [00:04:20]: Don't you even start with that.

Eric Ressler [00:04:20]: I'm just saying that's how they usually happen.

Jonathan Hicken [00:04:20]: Well, that's too bad because really if you've got a great strategy, you keep rolling with it as long as it's still working and as long as you're getting results.

Eric Ressler [00:04:30]: I'm half jesting, but honestly, that is often why a new strategic plan happens. But yes, let's say in the best case, it's time for a new plan. There's a pivot that's needed or the world has changed so you need to rethink the strategy. So yes, continue.

Jonathan Hicken [00:04:40]: Yeah. And look, we exist in this sector to deliver impact to somebody or something. And if we are not deeply in touch with their needs, their wants, their constraints, all of their factors, then why the hell are we doing a strategic plan to begin with? And your point about the leadership team is a good one. First off the board makes sense because hopefully your leadership team is plugged into...

Eric Ressler [00:05:10]: Doing that all the time.

Jonathan Hicken [00:05:10]: Is doing that all the time. Nevertheless, it was my top pick because I want to make sure that whatever change I'm making is going to be delivering better, faster, higher quality impact to that community.

Eric Ressler [00:05:20]: Okay. So you took my number two. Great. I think it's important to talk about the difference between influence and decision making power. And I think that's true actually for all of these. But for example, the community you serve, I think absolutely should have a major influence on your strategy, but I wouldn't put it out to vote. I wouldn't do a survey that's like, "Hey community, should we be this type of org or this type of org?" I would do that in the way that we do this work when we are doing data work or survey work or qualitative interviews with the community or the beneficiaries, we are getting those inputs and then we are synthesizing them with other people in mind. We're not asking those people to vote directly. In my opinion, some of the groups on this list should have more decision-making power. For example, I believe the leadership team should have a lot of decision-making power. The community should have a lot of influence, but I don't think this work usually works when it's truly democratic.

Jonathan Hicken [00:06:30]: Yeah. There's some pitfalls in even soliciting feedback from the community you serve. In my mind, I'm imagining a relatively large group of people, though there may be examples of smaller groups of beneficiaries, in which case the following won't make much sense, but you got to make sure that you're asking the right people, that you're asking the right questions, that you're going at the right time, that you're even using the right techniques to get in front of people. There's a lot buried in that in terms of getting the right input for the process. I agree with you. I've seen some pretty far outtakes recently about totally democratizing strategic planning, even down to things like budget spend. I think that's too far.

Eric Ressler [00:07:15]: I would agree. And if you look at even how our country is built from a governance standpoint and a political standpoint, because it's going swimmingly well right now, but nonetheless, we have a representative format. We don't just give individual citizens pure decision making power. And I think there's a balance there. Sometimes this gets to some of the most difficult parts about doing social impact work, which is like, who should hold the power in this work? And I could see a very valid counterargument to what I'm saying right now saying, "Well, why should EDs get to decide all of this stuff? Shouldn't it really come down to the community who is benefiting, who's getting the value out of this work?" And I would say yes to a degree, but also an individual's vantage point is going to be different, not better, not worse than someone who talks to a hundred of those people all the time. And so all of this requires some level of interpretation and synthesis. I agree that it can get taken too far and I've seen this happen with orgs that we've worked with before where they're almost afraid of their community, they're almost afraid of their staff to the point where they can't make decisions and just at some point make a choice, which to me feels like a not very effective way of being a leader.

Jonathan Hicken [00:08:35]: Yeah. This is the fundamental problem that you said right at the top, right? There is all of these inputs and all of them are important to some degree and just like having the wherewithal to prioritize them in a way that we're doing right now, which brings me, you've got your next pick.

Eric Ressler [00:08:50]: Yeah. Oh, it's my turn. Okay. I'm going to do a sort of controversial one. I'm going with my gut intuition Is my next pick.

Jonathan Hicken [00:08:55]: Ooh, okay. So you got leadership team and gut.

Eric Ressler [00:09:00]: So far all I've got is my leadership team and gut. I'm hoping to get some other folks on my team here, but I kind of looked at this wrong maybe from a game theory standpoint. I was like, man, if I could get my leadership team, the community in my gut, I'm solid. The rest, I'll get along on my vision. If I literally only had my leadership team in my gut, hey, I'll be honest, sometimes I am there in making decisions for Cosmic, right? I wouldn't probably recommend that if you're leading the Seymour Center or a community-based organization. I think sometimes gut level decisions get not as much credit as they should, because the body and the brain are actually really tuned to making complicated choices by intuition at a pretty good rate if you have the right inputs in your daily life. If you're just kind of like the kind of person who's going to listen to the last person you talk to, your gut's probably not the right choice. But if you show up in the way that allows you to constantly be pulling and getting these inputs, and then at the end of the day, you kind of just let your brain do its thing almost like shower thought style, I think it's actually really powerful. Some of my best ideas and my best choices have happened that way.

Jonathan Hicken [00:10:10]: There are levels to these decisions, right? I know that day to day I'm making sort of strategic level decisions from my intuition or with my leadership team and for the purpose of this exercise, we're kind of thinking of that transformative new strategy here.

Eric Ressler [00:10:30]: Okay. I'm going to say one more thing on this. I think most people actually do use their gut to make these choices anyway.

Jonathan Hicken [00:10:40]: And what? Don't admit it?

Eric Ressler [00:10:40]: Aren't even aware of it. And they use these other tools to reinforce the choice they already knew they wanted to make.

Jonathan Hicken [00:10:45]: Sure.

Eric Ressler [00:10:50]: I don't know. I'm putting the gut up high.

Jonathan Hicken [00:10:50]: All right. My next one off the board is data. Yeah. Look, it almost actually directly counteracts the gut intuition one, right? We have a saying at Seymour Center here where data beats opinions 100% of the time.

Eric Ressler [00:11:10]: Yeah, makes sense for science.

Jonathan Hicken [00:11:10]: Yeah. So I want to make sure that... I mean, you could break this down on all the levels. It could be financial implications, funding implications, staffing implications, community feedback, whatever. I need to have some evidence in quantitative format that where I'm going to head is going to build a stronger business and going to deliver more impact. And I need to see some evidence of that in some ways to almost activate my gut in a way. It's that affirmation that my gut is real.

Eric Ressler [00:11:45]: That's right. Well, and it's what you need to be able to make good gut level decisions. Oddly, you need data to make gut level decisions. So I'm actually really deep in a data focused project for Cosmic right now where I'm building out this internal app and dashboard that gives me visibility into my business. And what's been fascinating for me is that data is kind of like statistics where you can kind of mold and shape it in certain ways. And so you have to be careful because it's like, how good is the data? Because sometimes the data is really solid. It's been done by professional researchers or academics and other times the data is messy or incomplete or misleading. And so it can inform and influence you and steer you in the wrong way too, but you could say, well, the data says. And so all these things have a little bit of nuance, but I had data pretty high up there. I'm sad to see it go on my team.

Jonathan Hicken [00:12:40]: I think that we as EDs and CEOs, we need to learn how to read data because there's data that's predictive and sort of empirical and so ironclad that it cannot be scrutinized really.

Eric Ressler [00:13:00]: It's like self-evident.

Jonathan Hicken [00:13:00]: Right. In other cases, there's data that's directional, data that can give you a sense that you're within the bounds of the decision you want to make. And so when I talk about data, it's really more that.

Eric Ressler [00:13:15]: Yeah. I think that's a good way to think about it. That resonates with me when we're looking at engagement data for websites that we build or for campaigns that we've been part of where it's like you can get so lost in the nuance of like, well, the conversion rate did this one. And it's like, let's look at the trends, right? Let's compare it. Is it up or down month over month? Is it within a healthy threshold or baseline or benchmark that we're going for? So I agree that directional data is a lot more useful for these big decisions you have to make.

Jonathan Hicken [00:13:45]: All right. Who's next for you?

Eric Ressler [00:13:45]: Okay. So you took data from me. Although actually data wasn't next for me, data was a trusted consultant or strategist. Slightly self-serving take. I'll be the first to admit it. But again, let's assume trusted is doing a lot of work here. I think having someone who's not in the weeds all the time to give you that kind of fresh outside perspective is massive because if all you do is talk to your own team and even to a degree, talk to the community that you serve or talk to your board or peer organizations or people who are in this every day, you're going to get a lot of reinforcement that happens around like, oh, whether it's because this has been decided, this is the way or this is the intervention. And sometimes you just need someone to come in from a different perspective, an outside perspective who's like, "Well, we've worked with these types of orgs and they do it this way. Have you ever considered doing that?" To just have some new fresh thinking and input. So far my team is my leadership team, my intuition and a trusted consultant, they better be a damn good one. Luckily I still have some picks on the table, but I think that a trusted consultant, trusted, high quality, let's break down who might some of these people be: strategic planners or XEDs or people from, dare I say the business world, which is like this huge taboo in our space around listening to business advice, which you should be careful about. Design agencies like Cosmic. Who else would you put in this category that you'd be thinking about?

Jonathan Hicken [00:15:20]: Well, I would put you. I've had the pleasure of working with you on some strategic level projects and in that case, I think because you are trusted and because you produce quality work, that third party perspective was really influential and sort of in reality the way it played out became super influential in probably ways I didn't even expect. Now I think where you're coming from, correct me if I'm wrong, is really the value here of the trusted consultant is that they're just third party. They're distant. They have some emotional and just whatever daily distance from what you're talking about and I think there's an emotional importance to that. It's for that same reason that I'm choosing my board off the table next.

Eric Ressler [00:16:10]: Okay.

Jonathan Hicken [00:16:15]: Now there are a lot of caveats I'm about to put on the table about this selection and it goes back to one of our ground rules. We have to assume that these are trusted people.

Eric Ressler [00:16:25]: You're going to pick one of the 10 effective boards in the... No, I'm just joking.

Jonathan Hicken [00:16:30]: No, but honestly, right? I mean, we don't have to shit on boards right now and we all know that there is a varying degree of trust in boards and effectiveness in boards. So for me, when I take board off the table, what I'm imagining is a small group of trusted advisors who know your work but aren't too close to it and bring a variety of perspectives and a variety of talents to the table and serve as that sounding board.

Eric Ressler [00:17:00]: 100%. Real quick for listeners, definitely check out the spotlight interview we did with Rob Acton from Cause Strategy Partners who's, in my opinion, one of the world leading experts around how to design an effective board for nonprofits. And Cause Strategy Partners was the client of ours, full disclosure, but we learned so much about... I remember in our kickoff, I was like, "Rob, tell me how we can help our clients design effective boards." And he had really good answers for that and a lot of those are surfaced in the interview. The other thing I want to caveat around the board situation is back to that distinction around influence versus decision making power. Governance boards have a certain amount of decision making power that's kind of built into the structure, right? We're working with an org on a rename project right now. The board literally has to vote on that and will make a decision based on that vote.

Jonathan Hicken [00:17:50]: That's in their bylaws.

Eric Ressler [00:17:50]: That's in their bylaws, right? But in my opinion, boards should generally be less of deciders and more of supporters to staff. Rob touches on that to a degree and I think a lot of times where boards go wrong is they come in in good faith trying to do their work, but they think the way to do that is to help teach or influence or decide for the staff or they just get really tied to their opinion and think that it should have more influence than it maybe should. And that can happen at the individual level, it can happen at the board chair level, it can happen at the board level more broadly. And then you get into this consensus driven design by committee situation that just waters everything down. So I think board in the best of cases can be a super invaluable asset for all the reasons that you said and especially if they're there to support and guide, but are also able to detach and let go and trust staff and especially ED to make the final call.

Jonathan Hicken [00:18:50]: So for all of those caveats, that's why when I take board for my team, it is assuming all of those positive things.

Eric Ressler [00:19:00]: Yes.

Jonathan Hicken [00:19:00]: And I don't have a board.

Eric Ressler [00:19:00]: Right. Easy for you to stay here.

Jonathan Hicken [00:19:05]: Easy for me to say. Yeah. But you literally are a de facto board member for me. It's like you are the person I go to to talk about strategy and communications and messaging, et cetera, et cetera, et cetera. I picture you sort of like in this group.

Eric Ressler [00:19:20]: And you've got a collection of folks like me who are your unofficial board of directors basically, right? So you've got it kind of best of both worlds. You get all the free advice and none of the decision making. 

Jonathan Hicken [00:19:30]: Boom. Yeah.

Eric Ressler [00:20:20]: All right. I'm next, right?

Jonathan Hicken [00:20:20]: Yep.

Eric Ressler [00:20:25]: Okay. So I put peer organizations next. So far my team is my leadership team, my gut, a trusted consultant and some peer organizations. I'm starting to feel pretty good, but I do think that peer organizations, again, double edged sword, you have to be aware of the insider think here, but also I've learned a lot in my experience talking to other agency owners about like, "Hey, how do you track profitability by project? What's your formula? Can we just talk shop for a little bit?" And that kind of stuff is so helpful in a way that I've had consultants come in and try and tell me to do it a certain way and it's like, "Well, you've never run an agency, right?" That's an opinion, great. It may be valid, it may not be. So especially if you could, luckily for our listeners, you don't have to pick only five of these people, but if you could get that kind of peer level perspective of someone who's been in a similar seat as you and have seen a lot of the same challenges and have maybe overcome some of them who could share their learnings, their failures, that is invaluable. And at the same time, having someone who's a trusted consultant who maybe hasn't had that lived experience, but has worked in an adjacent space that can kind of cross-pollinate ideas, all of those inputs are really helpful. But to me, having that peer organization perspective, especially from another leader, especially from one who's maybe dealt with the challenge that you're dealing with can be just so helpful.

Jonathan Hicken [00:21:50]: There's another good reason that they should be on your team and that is they can sometimes be operational partners or collaborators, right? And so deeply understanding the whole ecosystem of work, what role everybody plays, where you fit in, where they fit in, where is the overlap, is your strategy taking advantage of the niche that you might be trying to fit into, right? So all of that input from peer organizations can create this win-win strategy that helps them too.

Eric Ressler [00:22:20]: Helps them too. And like you said, you may go in asking for input on your strategy and you may walk out with that and like a deal to create exponential impact. Okay. So what's your next pick?

Jonathan Hicken [00:22:30]: All right. Next off the board, just as a refresher, I have the community you serve, data, the board, and next off the board for me is major donors and funders. And there's the obvious reason, which is like, "Hey, if I do this new strategy, will you fund me?" And that's obvious, right? Obviously you're looking for a yes in that. I also think of it as like market research a bit where it's like, okay, I may have the most beautiful concept for a strategy, but if it's not exciting, if it's not solving problems that funders are trying to solve or that they care about, then this idea is dead in the water, right? This is dead before it even gets off the ground.

Eric Ressler [00:23:15]: If you are a social impact organization that relies on a lot of your funding to come from major donors or major funders, they are essentially another major audience of yours, another constituent that you need to serve at some level. We talked about this in a recent episode. There's a tension there around who should have decision making power and some of the pitfalls of going too far in terms of being donor led in your strategy. But I agree, you could have the best strategy in the world until someone's not willing to fund it, which honestly to a degree is usually because something's not penciling out if you're talking to savvy funders. Not always the case, but I think sometimes there's a lot of people just kind of like trash talking funders as being out of touch, but good ones are doing a lot of this kind of work, listening to their partners, listening to the communities that are partners serving and they have the ability to synthesize all those inputs so they may see a problem with your strategy that they've seen three other orgs try and fail that you aren't aware of yet, right? A grain of salt with all of that.

Jonathan Hicken [00:24:15]: They play that third party perspective in a way, kind of like going back to the trusted consultant thing, right? It's like they've got that perspective that they may be funding dozens of organizations and they've seen this before.

Eric Ressler [00:24:30]: Again, best of faith, these are like progressive trust-based funders. We're not talking about all the bad funders out there who are just objectively horrible at their jobs. Those exist too. And I would say that in a situation where you came to a funder and you had a new strategy and they gave you feedback that was counter to the direction you were going, a really good one would say, "Hey, let me pair you up with this org that already tried that so you can learn from them. And by the way, I'll fund an experiment in this direction instead." So it's not necessarily a no as much as it is again, like a support and there's always a tension there too because sometimes they may just call it wrong and your idea was great and they just didn't see it.

Jonathan Hicken [00:25:05]: I want to call out that my team right now has the community you serve and major funders donors because I think that a good funder is going to ask, what do the people that you're serving have to say about this? And they should be asking that question. So I got both of those on my team, baby.

Eric Ressler [00:25:25]: That's a little sad for me.

Jonathan Hicken [00:25:25]: All right, the last two on the board are frontline staff and public feedback.

Eric Ressler [00:25:30]: Okay. So if I'm interpreting public feedback as being not from the community that you serve, just kind of like general public feedback, I am definitely taking my frontline staff. And here's why I have them kind of low on the list. Some people who maybe are staff might feel a little sad about that. So a couple things. One, if I'm part of the leadership team, I should be listening to these people all the time. So rather than bringing them in only for a strategic planning session, and also sometimes the staff actually doesn't want to be part of these decisions, which I think is something that people don't think or talk a lot about. There's this movement to like be flat and democratic and everyone... And look, I've tried that a lot of times and we do that for certain things, but I've also learned sometimes that's actually a burden you're placing on someone who's like, "I didn't sign up for this, man." If I wanted to be the executive director, I'd be working towards that right now.

Jonathan Hicken [00:26:20]: Isn't that your job, bro?

Eric Ressler [00:26:25]: Isn't that your job? Why are you making me decide these things? This is above my pay grade and also maybe you're not actually paying me enough to even be carrying the stress of a decision this big where maybe even lives are on the line. So again, you have to kind of consider all of the context around this, but I do think the staff can have some good input absolutely and it just needs to be interpreted correctly because there are also cases where staff have really strong opinions and the loudest voice is not always the most accurate one. And sometimes I've seen EDs feel like, again, even afraid of what their staff is going to think about these choices. To me, that's a symptom of a deeper problem beyond just like you might be slightly off on your strategy.

Jonathan Hicken [00:27:05]: At the Seymour Center, the frontline staff are interacting with our visitors that are coming in the door. And so for me, when I went through this exercise of ranking, I chose the community I serve first and when I go to my frontline staff for feedback on stuff, it's to channel the voice of the visitor, right?

Eric Ressler [00:27:20]: You kind of cut in line.

Jonathan Hicken [00:27:25]: Exactly. Went right to the source. What are you hearing on X? And we can get that quick feedback. So it's not that I don't value the frontline staff feedback, it's that what I'm asking them for more often than not is what are you hearing from visitors? And I already took them off the board.

Eric Ressler [00:27:40]: Okay. So let's go through our teams then. So I've got my leadership team, I've got my gut, I've got a trusted consultant who's going to be a really good one, hopefully. I've got input from peer organizations and EDs and I've got my frontline staff. I feel pretty good about my team.

Jonathan Hicken [00:27:55]: So that's a pretty damn good team right there, dude. All right. So I've got the community you serve, my data, my board, my funders and public feedback, which we didn't really define or talk about real quick. That was basically like online, right? I think of social media immediately of like, what do people online have to say about my brand or my work or whatever?

Eric Ressler [00:28:15]: Yeah. Okay. So like the Instagram comment section, the Reddit threads, the op-ed comments that come in.

Jonathan Hicken [00:28:20]: That's it. Yeah.

Eric Ressler [00:28:25]: Let's put that down way low.

Jonathan Hicken [00:28:25]: Yeah, I know. So I feel like they're kind of dragging my team down a little bit more.

Eric Ressler [00:28:30]: Well, you got the community, so it's only fair.

Jonathan Hicken [00:28:30]: Yeah. And I mean, both of our teams at the end of the day, if we put your team up against my team and said, who's going to come up with the best strategy for X, Y, Z organization, I think there's an argument that both are positioned well.

Eric Ressler [00:28:45]: I think so too. And let's take this back to our listeners who now are like, "Okay, well, I don't have to only pick five people from my team, but I do need to figure out who do I listen to when I'm going to make big strategic choices? How much space or influence should I give them?" So I'd be curious to hear, how do you think about that when you're making choices as an ED?

Jonathan Hicken [00:29:05]: Well, you alluded to this earlier around the inputs that inform you. There's also the relationships that influence your thinking and of course then there's the deciding part. And really at the end of the day, I feel like my job is so much about synthesis. It's so much about understanding what's happening around me and it's about developing really trusting relationships that I can go and sort of make sense of the noise and that's really truly the sequence that it goes in, right? It's like, here's what I'm seeing, here's what I'm thinking, here's what I'm hearing, what do you think about that? So it really does factor in all of these inputs, but there's an element of, and part of it is just getting the reps in of knowing when a signal is a fit or not.

Eric Ressler [00:30:00]: Dare I say that you use your gut to make those choices. Isn't it kind of that?

Jonathan Hicken [00:30:05]: Yeah, I mean honestly though, right? But also it's the loudest voice in the room thing. You start to sort of pick up like, okay, hey, this is loud. And I want to understand if there's an important reason behind the loud, but I'm not going to just overweight the loud because it's loud.

Eric Ressler [00:30:25]: I think the other thing to acknowledge here is that sometimes there is just some politics, especially when it comes to the board or a major funder where it's like you got to throw them a bone or you might know this is the right choice, but you have to just do a cost benefit of like, is it worth fighting this battle at this moment? And for big strategic decisions, I would argue it is. But for other things, pick your battles. And ultimately that's maybe not the exact right language to use, but I would say that this is complicated work and I do think the way that we do this when we help guide strategy for clients is we do have an early inputs phase. Even when we're bringing a new client on, there is no bad document for you to send me. I want everything. I want to see what are the raw ingredients we have to work with here. I want the data. I want to know if it's good data. I want to know if it's bad data. We do interviews. I want to do sessions with the board. I want to do sessions with the community. I'm going to do my own audits. I want to just get everything. But then you do have to start to look for patterns, look for trends, look for energy that's like moving in a particular direction. And then towards the end, as you're coming down to making a choice at some level, you do have to just make a choice as a leader. You have to take all of those things and know that you're never going to make perfect choices, but you do need to take action. And that's the thing that I would recommend and that I get frustrated about the space sometimes is like sometimes I feel like we're actually really good at doing these input exercises and sometimes they're authentic, sometimes they're more performative, but we feel really good about that as a sector. But how much data do we really need before it's just like back to one of our old concepts, MVS, minimum viable strategy. You could plan forever, but the only plan that really matters is the one that you actually execute on. And when you start to execute on it, then you learn, then you iterate, then you keep going. So hopefully that helps listeners who are like, "That's a lot of inputs. What do I do with all of this?" I would say have discreet phases and containers for these things and be really clear with the people who you're asking for their time and energy. "Here's what I'd like from you and here's how we're going to use that." Because I think a lot of times what happens here is people think they have more power to influence decisions than they actually do or than you want them to and then they feel disappointed or angry or insulted when their vote didn't really count the way they thought it would.

Jonathan Hicken [00:32:50]: I think the power of finding a win-win is sort of underrated, frankly. When I get inputs from all of these sources, the way my brain is tuned is I'm constantly looking for that win-win, a decision or a direction or an action that's going to accomplish multiple stakeholders' goals at the same time. And that's A, to deliver more impact more quickly, more effectively, but also it is a way to get a quicker yes. Where if I'm coming to the table with a partner or a funder or whatever and I can clearly articulate why this thing is good for you, that's a quicker way to a yes.

Eric Ressler [00:33:30]: I think that's true. I think the near enemy of that is the trying to please everyone. I kind of have an internal gauge for these types of decisions that if literally everyone is happy, maybe the decision was too obvious and weak and there should have been a little bit more of a bold choice made.

Jonathan Hicken [00:33:45]: Yeah, fair enough.

Eric Ressler [00:33:45]: I don't think that's what you're saying. I just, for listeners, because I think honestly, what people often do is they do try to come to this situation where the board's happy, the staff is happy, the community's happy, everyone feels good. And usually that means you didn't take a big enough swing.

Jonathan Hicken [00:34:00]: Yeah. Let me be a little more nuanced in my position on that because the outcome I'm looking for when I look for that win-win is not the happiness scale. What I'm looking for is results, like business results or organizational results or whatever where it's like the funder and the partner, whatever decision I'm about to make is going to help them be successful as defined by their own organization's goals.

Eric Ressler [00:34:25]: So they might even disagree with the way.

Jonathan Hicken [00:34:30]: Exactly.

Eric Ressler [00:34:30]: But at the end, they can't argue with the...

Jonathan Hicken [00:34:30]: With the results, exactly. So it's not about finding emotional harmony. It's a cheat code almost that's going to unlock everybody's success. So anyway, for what it's worth.

Eric Ressler [00:34:45]: I like that thinking and I like the idea of just honestly being pragmatic around people are going to be influenced by things that benefit them. And so I mean, that's true for the community you serve. It's true for your funders. We talked about this in a previous episode where it's like understand your funder priorities and understand hopefully they're transparent about those things and they're consistent with them, which neither of those things are always true. But when you can get that, then you can figure out where is their authentic overlap and our mission and the things they care about funding, then you're off to the races.

Jonathan Hicken [00:35:15]: Yeah. So going back to how I started the episode of like, how do I answer this question? Really what I answer is, "Hey, I got a lot of feedback from a lot of people and I tried to find the strategy that was going to fit with all of those inputs."

Eric Ressler [00:35:30]: At the end of the day, what else can we do? This one was fun. We got to find more ways to do these tiering things.

Jonathan Hicken [00:35:35]: Yeah. We'd love to hear the listeners feedback on this too. You built a hell of a team, Eric, for your strategy input.

Eric Ressler [00:35:40]: Likewise.

Jonathan Hicken [00:35:40]: All right. Thanks so much.

Eric Ressler [00:35:40]: That was fun. If you enjoyed today's video, please be sure to hit like and subscribe or even leave us a comment. It really helps. Thank you. And thank you for all that you do for your cause and for being part of the movement to move humanity and the planet forward.