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Founders' Guide: One-on-ones

By Christopher Steiner  •  Jun 7, 2016

FundersClub reviews thousands of technology startups every year, and as a VC, has backed a global portfolio of top startup founders. Our insights come from our network of top startup founders and startup investors, and from our own experiences. Christopher Steiner was a co-founder at Aisle50, YC S2011, acquired by Groupon in early 2015.

The most valuable assets for nearly every startup are its team members. Like any asset expected to grow in value, team members and their careers have to be nurtured and maintained. Part of that means giving employees the proper work environment and compensation package, but the other part, the part that takes more effort from founders and executives, is serving as a partner to employees in helping them build skills, build a career, in helping them grow as a person. Founders who can do that effectively help themselves and their company as much as they help their employees, as the goals of the startup and the goals of employees have large overlaps.

Imparting leadership and guidance takes place every day inside a startup, whether that's through group meetings or general workplace chatter. In addition to that, many companies and founders choose to ensure of regular dialogue between founders and team members with regularly-scheduled one-on-one meetings. These meetings give founders a chance to speak directly about an employee's performance and the expectations for that employee. As a startup grows, founders who once had a hand in every important operation of a company grow farther away from some processes. One-on-ones give them a chance to keep abreast of progress and details they may not be able to scrutinize during the week. One-on-ones give founders the most calibrated measurement of employees' morales, their feelings on the direction of the business, and ways in which the founder herself might improve as a manager and leader.

Additionally, one-on-ones allow employees who aren't extroverted in team or company meetings a chance to say what they're truly thinking without worrying about the effects of groupthink. Team members can gain respect for a founder's methods, thoughtfulness and actions through these little interactions.

Not every company's one-on-one meetings will be the same, nor should they be. All of these things depend on the founder's personality, the business of the company, and how many employees are part of the team. But there exist certain rules to keep in mind when structuring one-on-ones. Here is a good reference framework for holding these little meetings that can define and maintain a startup's culture in a big way:

1. No distractions

Distractions should be banished from one-on-one meetings: founders should make it clear that they're not meeting with the team member out of convenience, but out of importance. This means keeping email, phone calls, and the minute-to-minute queries of other employees out of one-on-one meetings. Founders can be overrun, overworked multi-taskers, but one-on-ones demand 100% of a founder's attention. The meetings don't have to be long, but founders should ensure that they're wholly focused on the employee and the immediate conversation, much of which will pertain to an employee's career. Just as founders are running their startup, employees are running their careers.

2. Start meeting with structure, end with open agenda

Jessica Mah, cofounder and CEO at inDinero, which offers businesses accounting services and software, likes to dispense with numbers and key performance indicators early on in the meetings, as well as anything else that might be a regularly-scheduled topic during the chat. Once that's done, she leaves the back-end of the meeting available to open dialogue. She does one-on-ones weekly and likes to take them while walking around the block. "The walking gives us fresh air and less awkwardness, which equates to more creativity and brainstorming," Mah says. She adds that some of inDinero's seminal moments have occurred during one-on-ones, such as discussing the opening of offices in the Philippines and New York City.

3. Share agenda/notes

Maheesh Jain, cofounder and CMO at CafePress, recommends sharing an agenda for the meeting online with each employee, as well as notes from previous meetings, allowing them to add and edit. Focusing on KPIs during the first part of the meeting is natural, he says, but it's important to go back and look at past periods' notes and progress, charting things across longer periods and looking at what's been working across months and quarters for a particular employee rather than just the last seven days. "It's easy to get lost in weekly details and miss the forest from the trees," he says.

4. Talk about things outside employee's direct duties

At least a snippet of the meeting should cover things that aren't part an employee's job duties or directly adjacent to them. Team members should be allowed to address the big picture. They may see opportunities or issues with the business model, even parts of it unrelated to their role, that could be illuminative. Getting a wealth of perspectives is important. Employees observe the business closely, but from a different point of view from that of the founders, so they may spot things that you don't or to which you've been blind.

5. Be prepared to spur conversation

Anand Sanwal, CEO and founder at CB Insights, which tracks data on venture capital deals, says some people don't need much of a prompt to get rolling and talk about issues on their mind regarding their own career and the path of the company. But others aren't so forthcoming. In those cases, he likes to provide a list of questions, prior to the one-on-one, for the person to think about, picking out one or two to address during the talk. Sanwal's questions include:           

  • If we could improve in any way, how would we do it?
  • Who is really doing great work and kicking ass in the company?
  • Whom do you admire?
  • What’s the worst thing about working here?
  • What don’t you like about the product?
  • What do you love about the product?
  • If you were me, what changes would you make?
  • What accomplishment are you most proud of from the last 3 months?
  • What are we not working on that we should be doing?
  • Are you happy working here?

6. Follow up on the things uncovered in these meetings

Josh Pigford, the founder of Baremetrics, which offers an analytics layer for Stripe, stresses that founders need to follow up on conclusions reached during one-on-one meetings. "If you ask all fo these questions and then never do anything, you've missed the point," he writes. "You need to follow up and take action."

Pigford himself tracks all of his questions and answers from one-on-ones in an Evernote file. He checks in on the list regularly to ensure he's staying on top of the issues raised in the meetings.

Some founders like to schedule all of their one-on-ones on the same day of the week, with time set aside during the latter half of the day to follow up on to-dos kindled by the meetings. Building a company is never a tidy operation, but planning one-on-ones properly can push it a little more in that direction.