A More Human Job Search, Part 2: Preparing. Aligning. Shining.
people over job posts - so many get it backwards
If you’re here: check out part 1
Once you have a coffee chat or interview - now is your time to shine
Before you get started, get real with yourself on whether the prospect of working with the person or company is genuinely exciting to you. It’s about alignment.
Mindset:
Remember this isn’t an interrogation, it’s a two-way street, which is easy to forget in early career
Approach with curiosity and calm confidence, not desperation. If you need to wait until you’re no longer having desperate energy - wait.
Think of it as “exploring alignment” rather than “convincing them to like me.”
You want a conversation not a transaction.
First, don’t waste anyone’s time: These calls are not formalities, come prepared to talk about yourself clearly, your value add, what you’re looking to learn and next steps - own the process. Preparation is key.
Tailor a few bullet points explaining who you are and the impact you’ve had as it relates to the conversation. I can’t explain how many times I’ve been asked what are your 3 areas of expertise in a few or one word.
It goes without saying that in almost all cases, you’re the one setting up the call. Luckily, we have calendly, but if not, always suggest 3 times initially in your comms to avoid the back and forth and so the other person can align their time quickly:
“When would you be free?” is very different from…
“Do you have availability on Wednesday and Thursday between 10am and 12pm?” Especially for someone who has a busy schedule.
In my opinion…
How you do one thing - is how you do everything
Show how you work and operate - you’re selling yourself personally and professionally in every detail..
If I was meeting with someone at a company I loved and wanted to be a Chief of Staff or Marketer, I’d go back to my initial discovery process (mentioned here). Instead of making a company and then a person list, I’d just make a list of 5-6 people with my current or desired functional expertise before the call is scheduled.
Research the individual. Start with something you have in common from linkedin, articles, anything you can find and that you’re genuinely curious to learn more about. Choose a wide range of seniority. Those that can influence your experience and those early on - you can learn something from each one.
I’d ask them to describe their role and take copious notes. You’ll use this to craft your own convincing story with relevant industry verbiage (especially for pivoters). Take note of the words they use, pain points and most important aspects of the role.
Reach out and ask to learn about their experience, the company’s challenges, and what excites them. (Meanwhile, be crafting your story in the back of your mind.)
Don’t be afraid to ask hard questions, stop the process or say no - you’re looking for alignment not to tap dance for anyone nor have anyone tap dance for you.
For example, I was interviewing with a large PE firm and asked my interviewer an open ended question - would you say this role was operational or strategic? (I was looking for a more strategic role, but I didn’t ask that specifically because I didn’t want to be sold something that wasn’t there). I wanted an honest answer and reduced any leading questions. She told me the role was more execution and operational in nature. I then said, that’s great to know because I’m actually looking for something more strategic. I thanked her and told her it really wouldn’t be a good fit. She tried to sell me the roll every which way to the point of almost berating me for no longer being interested - I said, I don’t want to force something that doesn’t meet your needs, thanked her for the conversation and went on my way.
Not everything that calls your name is for you.
It’s okay to say, this isn’t it - my next thing might be around the corner.
The closer - At the end of each call I’d be sure to hit the following
Ask if there’s anyone else they’d recommend I speak to based on the discussion
Make sure I have relevant and thoughtful questions - I never like when I end an interview or coffee chat and the person has NO questions. Honey, there’s endless things you can ask if you really wanted to learn about the company/role with authentic interest.
Ensure that each conversation adds/builds your knowledge and isn’t just the same thing - again, this isn’t a formality if it’s authentic. For example, I spoke with Tyler about the xyz project, does your role intersect with that and if so, how? As you make you’re way across the company. You have no idea who is trading notes.
Track relationships - As you make your way around to the team, ensure to keep a running list of notes of each person you speak to and keep in touch on some sort of cadence depending on the relationship.
Show gratitude
Light touch: thoughtful thank-you email (reference something specific you learned).
Medium touch: handwritten card if they gave you significant time or insight.
Big touch: flowers or a gift only when someone went above and beyond (e.g., recruiter who literally landed you the role).
Follow your intuition and check in with yourself - did the conversations leave you feeling excited or drained?
Shoot me an email if you want my comprehensive list of questions to ask during coffee chats or interviews across individuals, team, function, and industry. mack.s.sasha@gmail.com. It’s important to leave no stone unturned.
💌
— Sasha Mack