3 Questions to Help Startup CEOs Have a Powerful Start to the Year

Alisa Cohn by

After the ball drops, after your team comes back from travel or hibernation, after you have your first leadership team meeting, it can feel like you’re playing catch up even before the year has really begun. Sure, you did some planning for the first quarter and yes, you will have a kick-off meeting. But, how can you really take advantage of the “clean slate” every new year brings? Ask yourself these three questions.

1. What is your theme for the year?

I encourage the startup CEOs I coach to come up with a theme for the year because it’s a great rallying cry for the team. Themes can also be great yardsticks. How does the team know what to do next or which project to focus on? Does one contribute more to the theme for the year? Pick that one.

One startup I work with spent last year focused on the theme of “learning.” That caused them to prioritize projects that would teach them the most. Yes, of course they sold to customers and fixed bugs and delivered new features. But they allocated time, energy, effort and money to thinking about what they wanted to learn and designing experiments to learn exactly that. They dedicated time to debriefing these projects so they could reap and share the learning and they consciously implemented their new knowledge.

This year their theme is “execution.” They are ready to start building stronger processes. They are structured to do what they know works rather than choose to do something off the beaten path to see what happens. This shift will determine their work plans for the year.

2. What are your “quick wins?”

One of the best ways to motivate people is to help them feel successful. A good way to do that is to set some very attainable goals that people can achieve in a short period of time. Yes, you need medium and long-term goals, of course! But medium and long-terms goals are made up of short “sprint” milestones and helping the team set these up consciously will drive a winning culture.

One of the CEOs I coach is the founder of a SaaS software company. One of the company’s goals for the first 90 days of the year is to redesign and implement a new pricing model. So far so good: that’s tangible and that’s very important for the company. But it’s a bit of a slog. It will take the fully 90 days to complete that deliverable. What is a quick win that someone can declare in the first month to help generate momentum and positivity?

The CEO talked with his VP of sales, and they agreed that the sales team would create two deliverables by the end of January: a top ten list of the common characteristics of their existing customers and an overview of what their competitors are doing.

These are necessary steps on the way to redesigning their pricing model. Framing them as “quick wins” helps people see where to start when they have a large and daunting project facing them down. Having a quick win to drive for helps them move fast. And when they achieve this and get acknowledgement for it they will feel good about their efforts. Also, everyone else in the company will feel good to be on the right track and part of a winning culture – pretty important given the ups and downs of startups.

3. How are your executives doing?

The beginning of the year is a good time to think about the team. Is everyone in the right roles? Are they performing at a high level? Have you given them feedback to help them grow and perform better?

Now, let’s be honest: do you have some executives who are not performing as you’d like? Are you starting to dread interacting with one of them? Do you keep wondering if this is the right person in this role?

The first quarter of the year is a great time for startup CEOs to step back and think about their executives.

Some steps to take:

  • Sit down with each of your key people and have an open-ended one-on-one to start off the year. How do they feel? How do they think they are doing? How do they think the company is doing?
  • Discuss expectations for the first quarter and for the year. Are they clear on your expectations of them? Do they know what success looks like? Do they have specific deliverables you’ve agreed on?
  • What are their career aspirations? What do they need from you to better support those? What specific feedback and suggestions do they have for you?

If you have any executives who you are concerned about, resolve that this is the quarter you will handle this. Have a heart to heart with them and share your concerns. Make sure the executives understand clearly your expectations of them. See if they need more or different support from you. If you don’t think they can change, create a transition plan. Having the wrong people on the team brings everyone down.

Think through these questions and add some more if you like. Ask your leadership team what they think are some key questions and topics to help make the most of the beginning of the year. Then create a plan with dates and timelines that you all buy in to. This way you can start your beginning of the year sprint knowing you have good structure in place.