Boost Investor Communication: Expert Insights with Executive Coach Sabrina Wang

So the 3 tips that I would recommend, the first one is actually very straightforward, is to just make an effort to create a social relationship. And I know a lot of founders already do this where they would structure something fun to do, something casual and social before or after the board meeting, usually after. And while throughout the quarter, throughout the year, the founders would reach out to the, the investor to try to get, grab breakfast, grab dinner, and get to know each other. And I even know that something that some founders do is to, uh, kind of bring their spouse and children and investors' spouse and children and try to get to know each other as family units. That's also very common too, because in order to create trust and psychological safety, you, the two people in any relationship needs to know each other as humans., so that tends to help a lot to, to be able to get into the habit of create that social relationship. The second one is very tactical that some founders are doing, which is when you send out an investor update, send it out in a, either a Loom or an audio message, something that gives in a voiceover of the email. That tends to help with communication because it adds this extra color to your wins or your fears. And the actual content of the investor update, I would encourage if there's some level of psychological safety there to put, honestly, here are our challenges and here is, here are what we're going to do and what our plans to tackle it. So the investors tend to feel a lot more comfortable when there are actual fears being shared and challenges being shared. If there are no challenges, That's obviously never true with a, with a company. So having a video and having these actual challenges written and recorded in investor update could go a long way. And the third tip that I would recommend is around the skill of making your investor feel heard. So what that means is investors come in and they have advice and perspectives. The number one skill that the founder can master is reflective listening and to say, hey, this is what I hear you say. I want to make you feel heard. Is that so? Before going into I agree, I disagree, here are all the things and go into solution mode. And that can be used in a one-on-one setting, probably the best before going into a board meeting. Let's say this founder wants to change their sales strategy from SMB to enterprise and they feel really excited about it, but they're a little bit fearful that they're going to get investor pushback, then it would be a fantastic idea to say, hey, investors, let's meet one-on-one before the board meeting. I'm going to share with you, this is my idea, and I'm just going to listen and make you feel heard. You're going to say, well, enterprise is really hard. It takes 9 months to close sales cycles, and I'm worried that you don't have the sales, great sales rep in, uh, in sight. And I'm just going to say, okay, well, let me get curious. Where is that coming from? I hear your concern. And then I'll say whether I have a plan for that or no, or I disagree or whatever that is. And even if the founder disagrees with something fundamentally with an investor, they can always say, hey, let me take your thought into concern. Let me take— let me think about it and then come back to you. And that all of those small communication tips will go a long way. So first of all, as soon as possible, I think the timing of it really matters. And, and with that, there's a granularity of as a CEO, as a founder, you have to first feel regulated first. Let's say if you're not feeling regulated, there's no point in rushing to calling the investor in 5 minutes. Let's take 10 minutes, 30 minutes, an hour, whatever it is for you to first feel calm. And then that fits into the as soon as possible window because that's a prerequisite. And then when you do share an uncertain news, it's a really good idea to write down what do you feel certain about. So I've worked with— I've heard about how people are handling SVB, but there are also a lot of scenarios where I've worked with founders where 30, 50% of their revenue goes poof because if something happens and they're at risk. So what I advise them and coach them to do is, well, what do you know that you're going to do? They'll say, okay, I have my CFO on board. They're going to run modeling for worst case scenario. This is the layoff. We're going to do a key man audit of if we do layoff, this is what it looks like. I know we're having a standup every day at 10 AM. These are the people who are involved and this is what we're going to do. I know that in 2 weeks we, we will know if we're actually going to lose revenue and this is what we're going to do, right? Like, and, and this is how much operating capital that we need and this is how much we have in the bank and this is how much runway we have. So we will actually create a list of this is what we do know. And that's really helpful to bring to an investor to say, this is what's happening. We don't know exactly what will happen, but here are all the things that we know for sure, and this is how we're going to tackle it. That tends to create a lot more confidence and certainty for the founder and for the investor as well. I would say the number one thing is to be aware of their own fears and concerns, because understandably, this is their investment and they have a degree of fear and, uh, their own reputation or whatever riding on this investment. So when they bring their own fears into the device, it tends to scare the founders, and that communication, that good intention and business acumen doesn't tend to get through. So I would suggest all investors, before they talk to the founder, to sit down and maybe even write down a list of what am I afraid of, what do I think is being unsaid? What is really happening at this company? And just check that a little bit. And beyond the fear, you can get down to what information do I need from this company, right? And then, and to be able to separate and talk about the content of the conversation and not so much the emotions of the conversation, that tends to just help it a lot more. And then secondarily, to be an investor who actually helps to say, hey, like, I know that you're going through this. I'm not judging you for it. This is very normal. Let's get down to brainstorming. That brainstorming phase when I, I've heard about some investor and CEO pairs, a relationship, and they say, oh my goodness, this investor is actually rolling up their sleeves to sit down with me to think about how to tackle this lead gen situation. And they're saying, I know this VP of marketing, I know this person, let me introduce you guys. And I want you to take this course. I know this other founder. So through brainstorming, they're making these connections and being very proactive. That tends to be the most helpful type of investors that I've heard of. I can expand on a little bit like the good, the great examples that I've heard that the CEOs say, oh, I have the best investors in the whole world, was when they, the CEO, he would feel like whenever something happens, I can call them up and tell them exactly what's happening. Oh my goodness, like I just lost 2 of my exec team and they were really good people. What the F is happening? And then investors would go, okay, tell me more about it. And they, the investor would not go into fear and think about, oh, well, what, what's wrong with the CEO? And they would say, okay, I trust you. I know the type of person you are. I've seen seen this dance before in all of my other companies, and this is what you can do. And they go, go into— and the investor actually would make the CEO feel heard before going into solution, and then they go into solution together, and they would be hugely productive. And on the flip side, there are investors who say, oh, I know, I know that the CEO is not fully trusting me, and that's okay because I know that it's not personal. There's a lot of things going on in the dynamics of this relationship, I'm going to recommend them a coach, a therapist, a consultant, and I want them to be well supported. And if not me, that's okay. I just need to know what they need and I'm going to send them these people. So as a coach, actually, we get a lot of requests from investors to get to know their CEOs, and that, that has worked well as well.