How To Cultivate “I like you, but…”

As a startup CEO, you’re going to meet a lot of people that you want to get involved in your company, but that you ultimately can’t. Examples:

1) Investors who like you personally and your business, but don’t yet invest.

2) Candidates and advisors you like you and the opportunity, but don’t yet join.

3) Prospects who like you and your solution, but who don’t become paying customers.

You will meet hundreds of them in the first couple of years of your startup. Most startup CEOs don’t do a good job cultivating these relationships. Here’s the quick and simple guide on how to do this in a few hours per month.

The first step is to track all of these people: use a CRM! You can use a personal CRM like StreakContactually, or an SMB-focused CRM likeRelateIQ. Manage the different classes of stakeholders with different tags or lists in the CRM. I wouldn’t recommend SalesForce for this purpose as SalesForce is overkill for the scope of effort here. The key attribute you will want is easy Gmail integration so you can add a contact to a list directly from your inbox to minimize workflow disruption.

The second step is to set aside 2–4 hours each month to do this. Just create a recurring calendar invite. If you schedule it now, it will be a priority. You will have time.

Cultivating Investor Relationships

In almost every blog post ever written about fundraising, one of the commonly repeated recommendations is to stay in touch with investors even when you’re not actively raising. The reasoning behind this is simple. Investors invest in lines, not data points. They want to see how a company progresses over time, and if the company can hit its stated goals. This also gives investors a chance to get to know you better to make sure there is a personality fit.

A common way CEOs manage this process is with regular investor updates and 10–20 minute follow up phone calls. A staggered quarterly cadence is best. Conducting 20–40 investor updates in a few-week span is too burdensome for CEOs. But spreading those 20–40 calls over 3 months into buckets of 6–13 per month is much more manageable. During each of those calls, CEOs should come prepared with one ask of each investor. Asking doesn’t hurt. The better the ask, even if the investor can’t help, the more the investor will like you for thinking strategically about the biggest sources of leverage. The best investors will help you even if they’re not invested. Cultivates the relationship per the Benjamin Franklin effect.

Don’t prepare fresh new content for these investor updates. No one is expecting a formal pitch deck. Instead, just share a handful of KPIs and graphs that they’re already using to run the business. You are probably already including these KPIs in your board meetings. The result is that the time burden of preparing these investor updates should be minimal.

Although this science is relatively known for managing investors, few CEOs do this well for other key stakeholders: candidates and customers.

Cultivating Candidate and Advisor Relationships

The process for cultivating relationships with candidates and advisors is remarkably similar. Candidates want to know the same basic things that VCs want to know: Are you growing? Is your business working? What are the key milestones you need to hit over the next 6 months? What are the risks? What roles are you hiring for?

Most of the investor update can be repurposed to be shared with candidates. As you grow, the diversity of your candidate base will increase. So you’ll want to add in content to appeal to technical types and not just business people. You won’t however want to hop on a phone call with each candidate. There will simply be too many who aren’t ready to leave their current jobs. Your candidate hot-list will swell to over a 100 quickly. There’s simply no way to have that many conversations on a regular basis. However, it’s probably worth it to hop on the phone with your top 3 favorite candidates. You want to stay top of mind.

As your startup grows and you hire capable VPs, you’ll want to pass this responsibility onto each VP. VPs can cater the content to be geared towards their respective audiences. The VP content should include a general note from the CEO as it will make the candidate feel good.

If you have 5 VPs — Sales, Marketing, Engineering, Product, Customer Success — who each own a hot-list of 30–50 candidates, that means you’re actively engaging 200 candidates each quarter. That’s a big deal. Hiring even just a few of them will make a huge difference in your business. And even bigger deal will be that those VPs will engage the 3 best candidates in their respective areas. Hiring even one of those top 15 will be a huge boost.

Cultivating Customer Relationships

CEOs should own this function for all relationships she personally establishes even past $10M ARR. In the early days, the CEO will lead every customer phone call. You’ll build relationships with lots of early potential customers. There will be a select few — typically the most sophisticated, the one’s that “get” your product almost instantly, but that aren’t interested in becoming customers today for one reason or another. Those are some of the best people to stay in touch with. They probably like you and want to see you succeed, but just can’t engage as a customer just yet. These can be some of your best advocates other than paying customers.

The message to potential customers should be very different than the messages to investors and candidates. Customers care far less about the state of your business and much more so about how you can help them. Give them some general information about the state of the business: e.g. “We grew 25% last quarter” even if they don’t know the base from which you grew. Or “We made 2 key hires: Joe and Bob.” But more importantly, highlight, if you can, customer success stories! And share new features thatmatter and explain how they will extract value from those features. Make sure this email doesn’t feel like a newsletter. It’s not. It’s a personal note from the CEO to a really important prospect.

It’s likely that this list of customers isn’t that large. So this may be something you want to individualize on a per customer basis. If you really really really wanted that person to be a customer, they are worth an extra 5–10 minutes of your attention each quarter to deliver a personalized message. And of course, ask for a 5–10 minute phone call to catch up.

That’s it! Cultivating existing relationships is one of the lowest-hanging fruits that you can pick. It’s not hard, but something that most forget to do when they’re caught up in the daily grind.