4 Ways To Avoid Getting Blindsided By An Unhappy Employee

When you’re launching a startup, the last thing you need is for a key person to bail out unexpectedly. Here’s how to avoid having that happen–or at least be prepared if it does.

4 Ways To Avoid Getting Blindsided By An Unhappy Employee
[Image: Flickr user Anders Sandberg]

You’ve started building your product and have raised a seed round of funding. You feel great about your progress and are ready to take on the world. You start hiring and add three employees to your team. Now your business is really growing and the future looks bright!


And then, bam!–your lead engineer decides he’s not happy. He used to be responsible for coding and product design, and he loved this role. But since you hired a dedicated user experience person, your lead engineer doesn’t lead product anymore. Instead of designing and building product, now he’s just building. And he doesn’t tell you he’s unhappy until it’s too late–he’s already accepted a job at another startup.

Now you’ve just lost a key employee, which you never saw coming–and it’s your fault.

If you think this could never happen to you, you’re wrong. As CEO, you are responsible not only for keeping your customers happy, but also for keeping your employees happy. To hold onto your employees and make sure they’re satisfied with their jobs, you need to change the way you seek feedback from them.

Below are four critical lessons I learned as CEO of Magoosh to avoid employee dissatisfaction:

1. Stop asking leading questions

Many employees, despite their best intentions, don’t feel comfortable telling a founder or CEO that they aren’t happy at work. When you ask leading questions like “You’re happy, right?,” your employees will be unlikely to say anything other than “yes.” You’ll feel great–until you’re blindsided with their resignation letter. Instead, ask open-ended questions, such as “What about your work keeps you up at night?” or “What part of your job do you enjoy the least?” These questions will help you get honest answers, and even if you can’t address the issue immediately, you’ll have a better sense of the state of your team’s morale.

2. Hold regular one-on-ones

I meet with all my direct reports every week for 30 minutes. In these meetings, I provide feedback for my employees, but I also ask them for feedback. I have a regular opportunity to ask open-ended questions to my team and get a sense of how they feel about their job. The one-on-ones serve as a forcing function for me and the employee–we have to meet; there’s no way out (it’s on the calendar). And even if three out of every four meetings consist mostly of small talk, it’s still worth it to meet weekly for that one eye-opening meeting.


A few years ago, an employee mentioned during a one-on-one that she was thinking about exploring new opportunities in a few months. Because I had regular check-ins with her every week, we were able to keep a running dialogue about this over several weeks. I was able to understand why she wasn’t happy and right the ship.

3. Have unhappy employees write out their ideal job descriptions

When the above-mentioned employee was thinking of leaving, I had her write out her ideal job description. I asked her which projects she wanted to continue working on, which projects she wanted to stop doing, which new projects she wanted to try, and what her ideal salary was (keep in mind that it’s often not about the salary but about the nature of the work itself).

Having her write an ideal job description helped both of us pin down the reasons for her dissatisfaction and figure out what needed to be done to make sure she was happy at work. Another way of going about this is to ask, “What are the things you are doing today that you don’t want to be doing in six months? What are the things you do want to be doing in six months?”

4. Use anonymous feedback tools

Some employees don’t feel comfortable providing in-person feedback, so it’s your job to find other ways to get feedback from them. Here at Magoosh, we use TINYpulse, an easy-to-use tool that sends a one-question survey about company culture and happiness to our team every week. Within TINYpulse, employees can also share feedback anonymously. I can respond to the anonymous feedback, and the employee doesn’t have to reveal his or her identity. Oftentimes, after people have provided their feedback anonymously, and I’ve responded to their comment (hopefully, in a friendly way), they’ll come forward and discuss their concerns with me face-to-face. But without the initial anonymous feedback, we would have never had that in-person conversation.

Getting honest feedback is scary, especially if you’ve never done it before, because it’s like opening a Pandora’s box. But after you have a handle on it, you’ll be able to stay ahead of any team issues and keep your employees happy.

Bhavin Parikh is CEO and cofounder of Magoosh, a company that creates web and mobile apps to help students prepare for standardized tests such as the GRE and GMAT. He loves advising startups on growing their ideas and building great cultures.


The Young Entrepreneur Council (YEC) is an invite-only organization comprised of the world’s most promising young entrepreneurs. In partnership with Citi, YEC recently launched StartupCollective, a free virtual mentorship program that helps millions of entrepreneurs start and grow businesses.