Red Flags & Green Lights: Derek Johnson's Guide to Startup Interview Success

In our latest Wellfound Community "Ask a Recruiter" session, Derek Johnson, a talented acquisition leader and self-proclaimed "Candidate Experience Defender," shared candid advice on navigating the interview process from both sides of the table.

With extensive experience scaling technical and go-to-market teams across high-growth startups from Series A to Series C at companies including Cartwheel, Octave Health, WorkRamp, and Chili Piper, Derek brought a refreshingly transparent perspective to the challenges job seekers face.

Watch the full video of the Q&A here:

TL;DR: The most successful candidates evaluate company culture by examining how values are actually demonstrated, use behavioral questions to interview the interviewer, strategically present ownership in discussing failures, and find creative ways to highlight skills gained during career gaps. In today's competitive market, standing out requires personalized outreach beyond standard applications, including video introductions and leveraging your network.

Finding Opportunities for Real Growth

Everyone claims to support career development, but how can you tell if a company truly offers growth potential?

"One way that I've done this and one way that I love seeing candidates do this to me as a recruiter is, heading into that search, heading into that interview, doing your research on the company,"

Derek recommends looking for employees in similar positions to the one you're applying for and seeing if they've advanced within the organization.

During the interview process, ask behavioral questions that reveal how the company actually supports growth. Derek recommends asking hiring managers: "Provide me a time where you helped a team member of yours navigate the next step of their career. How did you enable the upward mobility that the team member was looking for?"

This question forces the interviewer to provide concrete examples rather than generic statements about growth opportunities.

Avoiding Toxic Workplaces: Warning Signs That Matter

To assess a company's culture before accepting an offer, Derek suggests leveraging behavioral questioning techniques—the same approach recruiters use when interviewing you.

"What I'll say instead of like, 'tell me about the culture of the company,' I'll say, 'I noticed that the company lists that their values are X, Y, and Z. I really love this value that was posted on the website. Can you tell me about a time where this X value showed up for you as part of the company and how was that demonstrated?'"

If they can't readily share examples of how their stated values manifest in daily operations, that's an immediate red flag.

Another critical evaluation point: "Take inventory of the interview process that you've gone through." Consider whether the process made sense for the role, if you were given opportunities to showcase relevant skills, if the questions aligned with the job, and if interviewers were prepared and respectful of your time.

When evaluating startups specifically, Derek recommends asking about:

• Financial runway
• Major upcoming investments and initiatives
• Product roadmap highlights
• Recent customer acquisitions

Presenting Your Best Self: The "Tell Me About Yourself" Question

The dreaded "tell me about yourself" question is your opportunity to make a strong first impression—and Derek encourages candidates to embrace it.

"I was once told by a hiring leader, when you're interviewing, that's your time to be modest or not be modest. That's your time to actually brag and brag well and do it in an artful, tasteful way."

Derek recommends this structure:

1. Start with brief personal details
2. Explain why you're interested in this specific position
3. Highlight relevant experience that has prepared you for this role

Keep your response under three minutes and remember the context—avoid diving too deeply into personal hobbies or details that aren't relevant to the professional setting.

Owning Failure: How to Discuss Unsuccessful Projects

When discussing past failures, Derek emphasizes one key principle: ownership.

"Being able to know, like when somebody says, 'tell me about a weakness or a time that you failed,' owning that there was this project that I worked on where I failed...don't be afraid to call it a failure, but then talk about what steps did you take that caused you to fail."

The formula for turning a failure discussion into a strength:

1. Honestly acknowledge the failure
2. Identify what went wrong
3. Explain what you learned from the experience
4. Describe how you've applied these lessons since then

Navigating Employment Gaps Effectively

Gap periods in your resume don't have to be liabilities if handled with transparency and creativity.

"If you took a year off to be a parent because your kid needed you for the last year or the last three years, own that,...But then also when it comes to gaps, don't be afraid to be creative."

He recommends highlighting skills or knowledge you gained while away from traditional employment—whether through self-study, volunteer work, or personal projects. "If you literally took a gap to focus on your mental health and wellbeing, I'm pretty sure there is something that you taught yourself as a skill."

For resume presentation, include a brief explanation of the gap with any relevant activities or skills developed during that time.

Standing Out in a Competitive Market

With hundreds of applications for each opening, particularly at high-growth startups, how can candidates rise above the noise?

Derek acknowledges the challenge: "The competition is stiff and it is." His advice centers on personalization and networking:

1. Target your application: Ensure your application clearly addresses the minimum qualifications for the role
2. Leverage your network: Find connections at target companies who can provide referrals
3. Personalize your outreach: Research specific team members and customize your messages
4. Consider video introductions: Send short videos introducing yourself and highlighting relevant skills
5. Find email addresses: Direct emails often get more attention than LinkedIn messages

For career-changers like those transitioning into software development, Derek recommends building a portfolio through bootcamps or independent projects that demonstrate your skills. "Finding people who are in the positions that you want to be in...grabbing coffee chats with them, learning about what they do every day, building connections, building rapport" can provide both knowledge and champions for your job search.

Actionable Takeaways

• Test for authentic values: Ask for specific examples of how company values are demonstrated in day-to-day operations to assess if they're truly lived or just marketing language.
• Conduct a "reverse interview": The interview process itself reveals a company's organization, respect for candidates, and attention to detail - use it as a data point in your evaluation.
• Embrace professional bragging: Interviews are your time to confidently highlight your achievements in a structured, relevant way without veering into arrogance.
• Transform gaps into assets: Reframe employment gaps by highlighting the skills, knowledge, and perspective you gained during those periods rather than trying to hide them.
• Personalize your outreach beyond applications: In today's competitive market, differentiate yourself through personalized messages, video introductions, and building relationships before applying.

"The interview goes both ways. They're just a person on the other side. I'm just a person. I'm here to help facilitate you through the process. I don't want you to lose. I want you to win. A good recruiter wants you to win." - Derek Johnson

This article summarizes key points from Wellfound's 'Ask a Recruiter' live Q&A event featuring Derek Johnson. To learn more candidate tips, check out other 'Ask a Recruiter' sessions on the YouTube playlist here.