Sprint to a New Job in 2025: Week 4

This issue is published in sponsorship with Wynter! Wynter is a market research company and I’ve made 4-figures doing market research surveys and studies through them over the last few years! They are particularly excited to add more HR and marketing folks to their platform given the kinds of research requests they’re getting.

P.S. Here’s a video I made that shares more about it.

Starting 2025 off strong!

Welcome to week 4: Interviews!! This week, I’m going to share a bunch of awesome tips for

Here’s what’s ahead for the rest of the year:

Week 5: Compensation and Offers

Week 6: A final wrap-up/remaining questions that have emerged from you all!

Make sure to submit your questions as well - I’m going to cover at least 2 per week!

If you think this sprint will be helpful to your network, invite them!

But first, some resources

Before we jump into advice, let me highlight a few resources:

1. Of course AI has entered the interview space! Google’s AI warmup (free) will record your responses and give you feedback so if you’re feeling nervous, this might be a good starting point.

2. I crowd-sourced an interview question bank a while back. You’ll likely encounter questions like these in any interview process so thinking through responses could be helpful.

So let’s dive into the interview process!

To begin, let’s dive into what you can expect, and what we’re looking for at each stage.

Recruiter Screen

Most corporate/tech processes are going to begin here. At a minimum, a recruiter screen is looking to vet your minimum qualifications.

• We are gauging basic fit with the role and company. Why do you want the job, do you know what the company does, have you done the kinds of things we’re looking for in the role? People get annoyed by questions around why you want the job but the reality is that companies want to bring someone on who is passionate about their work and candidates need to convey that.

• We will try to better understand the scope and scale of your work, where you sat in the org, etc. This is because we know that people can have the same job title but do vastly different things, and we want to see how your experiences translate to our context.

• We will want to vet some basics like compensation and timeline to make sure that there’s alignment on both ends.

• We may ask a few behavioral type questions that align with company values or one of the major initiatives needed in the role.

How to prepare: I would prepare your elevator pitch - a 60-90 s overview of your resume where you highlight a few big achievements that align with the role, and be ready to share an experience or example that aligns with each thing listed on the job posting. You will also want to review the company website - read a few blog posts, read the values, know what the product does.

The biggest mistakes I see: Often it’s not on the candidate! It’s that we get on the screen and the experience simply isn’t as aligned as we hope. But when people do misstep, it’s often showing they aren’t super invested. For example, they ask basic questions that are communicated clearly on the website (“what does this company even do?”) or they don’t offer a compelling reason for their interest (“honestly I just wanted a remote job”).

Hiring Manager

Most companies will connect you with the hiring manager after the recruiter screen. These interviews are frequently going to be behavioral in nature meaning they want SPECIFIC examples of a time when you did the thing they are asking about. What the interviewer than does is pull out from that what behaviors you exhibit in those situations.

You’ll want to share the Situation (context), Task (goal), Actions you took, and the Result. It’s always helpful to be ready to share a reflection as well on how you might do even better in the future. You’ll often see this referred to as the STAR Method.

So for example, if they ask for a challenging situation you encountered in working towards a goal, you might share an example like:

S: I was planning a week-long onboarding training for 100 new employees. It was our first time doing this training virtually due to the pandemic. I had just a few weeks to make this shift, and had identified and implemented a new webinar platform to manage the training. A week before the training, the platform let me know that they needed everyone loaded in with their company email 7-days before the kick-off and needed this info from us, and our IT team didn’t do this until 48 hours before a new employee started.

T: I needed to address this issue to ensure that we had everyone in the system to start our kick-off on time.

A: I took ownership and let all the players know that I’d missed this deadline. Given that I had 24 hours to resolve this, I wanted to first look for points of flexibility. IT let me know it took them a minimum of 48 hours and they didn’t have the capacity to move on this right away. I went to our new webinar platform, and asked for flexibility and was able to gain an extra 2 days. I then worked with my department leader to identify capacity to support IT to speed up their work. I was able to reprioritize my time and another team member leaned in so we were able to get all of the new hire information into the right format to hand off to IT. As a result, they were able to get folks into the system by the adjusted target.

R: The onboarding went off as expected! We had just 1 technical issue that had nothing to do with our company, and 97% of participants were satisfied with their onboarding experience, which actually exceeded our in-person onboarding results!

R: In reflection, I wish I had better understood these requirements in advance. While they didn’t highlight this during the sales process, I could have asked more questions. It was my first time working on an RFP and new vendor, and I realize now that our project plan wasn’t as comprehensive as it could have been. I codified these learnings and actually created a guide for others in my organizations when implementing new tools so it’s helped others get ahead of these sorts of issues, and I used this in my own implementation of a new LMS last year. I also gave feedback to the vendor that it would be helpful to communicate these requirements up front. I noticed the following year, this was on their checklist for our onboarding so I appreciate that they took the feedback too.

From this example, the hiring manager can see that you’re someone who takes ownership for mistakes, that you are able to work cross-functionally and manage up to your manager, that you get creative about finding extra capacity, that you aren’t afraid to ask for help. Through the reflection, they can see how you learn from those mistakes, and set up systems to prevent them in the future, and that you share those learnings. They care less about your specific example (though ideally it’s relevant to the work you’re applying to do!), and more about what behaviors you show and how that translates the behaviors they hope to see.

Other Hiring Manager interview tips:

• Know your metrics. Be ready to give specific results and outcomes in your work.

• Bring strong questions around the team’s work, strategy, etc. This is your chance to learn exactly what they are looking for in this role, and hiring managers appreciate someone who is curious and shows genuine enthusiasm around the role.

• Focus on the two-way relationship as well. This could be your next manager so getting a sense of how you’d work together is important.

The biggest mistakes I see: People speak in generalities (“when faced with a challenge, I will dig in, work hard, and be flexible so I can achieve my goals, I’m just that kind of person that never takes no and always gets a good outcome!”.

Skills Assessments and Stakeholder Interviews

After the hiring manager, you will typically move on to a loop of interviews that may include take home assignments, presentations, panel interviews, meeting with stakeholders, etc.

In these stages, you’re more likely to encounter scenarios (see tips here) or be asked to show how you’d do the work. You could be asked to provide work samples or to do a small project.

This can really run the gamut and depends on your industry and field, so my best general advice:

1. Have a portfolio and work samples ready that you can send off without much effort. If you’re currently employed, save those things for the future!

2. I know folks have mixed feelings on doing projects for an interview. Personally, I love them. I like to be able to show what I would do, and it also gives me insight into the work. And particularly for a super desirable job, they want to feel confident you can actually do the work. Of course if the work feels exploitive in nature, don’t do it. But most project should take under an hour and are really intended just to see how you would approach the work vs steal your labor. (And realistically, you won’t have the context to create anything super useable in that time anyway!)

3. If they DO ask for something unreasonable, it’s OK to politely push back. I’ve seen these assignments get changed in the past. For example, you could ask if you can provide a work sample instead of creating something new.

4. Don’t be afraid to ask questions to understand what they’re looking for before you get to work. You can also ask what they are looking for. Is it creativity? Is it presentation skills? Is it about the content? This can help you know what to focus on.

The biggest mistakes I see: Honestly, this is a big drop off point and many folks just decide not to follow through at this point. Often, it becomes clear that while someone could say the right things, the technical skills aren’t there in terms of writing ability or analysis or whatever is being assessed.

Executive Interviews

Finally, many processes wrap up with an interview with a senior leader. Often, they are less focused on the day-to-day work and more about the caliber of talent coming into the company. They may be curious about your vision for the role, how you align with company values, etc. These are also folks who are deeply invested in the company and have often been there for a long time, and therefore, showing that you really want to be a part of what they’ve built can go far.

The biggest mistakes I see: At this stage, it’s often less about mistakes and more about luck in many cases. Perhaps someone was a touch stronger. But if there are missteps, it’s often not making a case for how the company will be better as a result of hiring you. Make sure you really show off what you bring that no one else does.

And a final tip…

Remember that recruiters are your support during these processes! Don’t be afraid to ask what the interviewers are looking for in each interview, why people have struggled, what problems the team seeks to solve with this role, etc.

We are here to help and want you to be successful - so use the recruiter to help you in your preparation!!

So, by the time you receive next week’s issue, I would encourage you to:

1. Draft out a few great stories/examples you can pull from for behavioral interviews.

2. Work on your "elevator pitch” for when they ask you to walk through your resume.

🙋Answering Your Questions🙋

Each week, I’ll answer one (or more!) of your questions in this section. You can submit your questions here.

These are the hardest situations for sure! Personally, I wouldn’t blame the manager, and my advice is usually to be forward looking. “I’ve enjoyed my time at company X, but I’m looking to be a part of a team that’s a bit more collaborative than how we operated” (or whatever aligns with the opposite of the issue you encountered!)

You can also lightly allude to the issues. “We’ve had a lot of transitions on our team and I’ve stuck it out since I know my manager has been struggling, but I also want to make sure I’m not sacrificing my own growth for the good of the team. This role just seemed like such a strong fit that I wanted to explore it.”

But holistically, my advice is to focus on what you are running towards instead of what you’re running from.

Ugh, this is always heartbreaking since you’re SO CLOSE to the finish line.

You can always request feedback, but the hard thing is that it often comes down to really minor things - or often, nothing at all and simply the fact that someone else won them over a bit more.

A few ideas:

1. If you’re interviewing for more senior level roles, I think this is the chance to operate like you’re in the role. Cast vision for what you’re going to accomplish and really give them the confidence that you’re bringing a strong vision and strategy to the company.

2. In general, I think companies are using these last interviews to confirm that the person can solve whatever problems the role is intended to solve. Show that you really understand the core issues and are excited to tackle them.

3. They often want to know how you’re going to level up the team. Be ready to highlight how you work to achieve goals, solve problems with creativity, etc.

Finally, you might reach out for feedback if you haven’t already done so to see if there’s anything with in your control that you can address.

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