The Career Changer’s Guide To Informational Interviews: How To Find Clarity, One Conversation At A Time

An informational interview

Informational interviews are one of the most powerful tools you can use to move your shift forward. But how do you find interesting people to speak to? What questions should you ask? And if you don't have any career ideas yet, how can interviews help you get inspired? Here, Natasha shares the most important things you need to know – and the mistakes to avoid.

Whether you think you know what you want to do next in your career or you have no idea whatsoever, there's one thing you need more than anything else.

Facts.

Whenever a career idea crosses your mind, it brings with it a whole list of unknowns.

  • Won't you have to retrain?
  • Is it all it's cracked up to be?
  • What's the pay really like?
  • Is it even possible for someone to move into that field with no experience?
  • How long will it take to make your way back up the career ladder?
  • What haven't you considered?

And not having answers to those questions keeps you stuck inside your head, chasing your tail, feeling lost and alone.

What if you had a chance to ask anything you wanted of someone who had real-life experience in an inspiring field?

To grill them about the realities of the industry, and find out exactly what you needed to know?

To listen to their day-to-day and, from that, get new insights into what you respond to with excitement and what simply doesn't float your boat?

Welcome to the informational interview: one of your most powerful career change tools.

Informal, insightful conversations with 'insiders' working in an industry you're excited by.

Done right, an informational interview will:

  • Give you valuable insights into the reality of an industry
  • Connect you with people of influence at organisations that inspire you
  • Energise and motivate you when you’re feeling lost or uncertain
  • Give you access to a broad community of people who are doing what they love

Some informational interviews might be brief conversations that give you a single insight, and you never hear from the person again.

Others could be the initial spark of friendships that last for years.

And a few will start the process of opening a door into your new career. When your CV is more likely to be a hindrance than a help as a career changer, the personal connections you make are priceless in terms of your ability to bypass job applications and be the first to hear about new opportunities.

Whatever forms your conversations end up taking – whether they're the source of disappointing realisations or lifelong love affairs – every interview you have will give you an insight into the world of the career you're considering.

And if you don't have a career you're considering – if you're just floating in a mess of 'I don't know' – then starting to have conversations with anyone who does something that piques your interest will give you real-world, gut-level insight into what you like, what resonates with you, what makes your ears prick up, and what doesn't.

So if you're stuck under a mountain of uncertainty, not knowing which way to turn, it's time to give the informational interview a try.

Here’s our beginner’s guide:

How to find people to interview

So, this informational interview thing sounds great.

You'd love to have the chance to bend the ear of someone who's in your dream industry; to have their undivided attention for a while, and ask all your burning questions.

But how in the world do you find these inspiring people? And what in the world would make them take any interest in speaking to you?

There are four main categories of potential interviewees:

  1. The Oh-Gosh-Of-Course
  2. The Meet-My-Friend
  3. The Since-You're-Here
  4. The Big-Wonderful

1. The Oh-Gosh-Of-Course

It's amazing how often our most useful connections are the closest to home.

Chances are, there's someone in your immediate network (family, friends, old work colleagues and acquaintances) who has something to do with the industry you're interested in.

And all it would take to find them would be to ask.

An email, a phone call, a post on social media… “Do I know anyone who works in X?”

When Alison took part in our Career Change Launch Pad, she never dreamed she'd be so clear by the end of the eight weeks where she wanted to be.

And her greatest insight came from speaking to someone she'd known for 16 years, who had studied (and was now working in) exactly the field Alison is now shifting into.

They had been great friends for a decade and a half, but had never really discussed anything to do with work.

A true “Oh gosh… of course!” moment.

Alison reached out to her immediate network to see if she knew anyone working in one of a list of potential career paths. In the space of three months, she had over 50 informational interviews – and it all started by reaching out to the people she already knew.

One person put her in touch with another, who put her in touch with another, and all she had to do was keep saying 'yes'.

Who do you know that works (or has worked in the past) in an industry that interests you? Start with them.

2. The Meet-My-Friend

If you don't know anyone directly working in a field you're inspired by, it's almost certain that you know someone who knows someone who does.

Evolutionary psychologist Richard Dunbar estimated that each one of us can maintain a social circle of around 150 meaningful connections with people at a time. That's about 150 people you could reasonably call on for an Oh-Gosh-Of-Course connection.

Next, consider that each one of those 150 also each knows approximately 150 people, making the total number of people you could speak to, simply by way of an introduction through a mutual friend, around 22,500.

And then look me in the eye and tell me you don't have access to anyone who does something inspiring.

Again, an email to friends or a post on social media can be a great way to tap into these wider networks…

“Do I know anyone who knows anyone who works in X? Would you be willing to put me in touch?”

How many people's networks could you tap into with a quick email request?

3. The Since-You're-Here

Most of the time, once you've spoken to a few friends and friends-of-friends, you'll find yourself receiving offers of further introductions to more people.

But there may also be times when the thread of connections and conversations runs out.

And if and when that happens, you'll need to tap into the Since-You're-Here kind of connection.

People who share interests tend to spend time in the same kinds of places.

You'll find artists and creatives at art classes, for example, or galleries. You'll find tech-heads at technology meetups and events. You'll find mindfulness and well-being experts at health and wellness conferences.

Take yourself to those same places. Start conversations. Have mini-informational interviews there and then, or use those conversations as springboards to build relationships for later.

Most of the time, the people you need to know are already somewhere in your network.

And when they're not, all you need to do is go out and find them.

Where might people who share your interest hang out?

4. The Big-Wonderful

There are some people who simply aren't in your network, or your network's network.

They're often the big hitters – the business founders and the campaigners, the TED speakers and the award-winners.

Or maybe they're the minor celebrities that only you really know about, because the industry you're excited by is pretty niche and not many people are such giant fans of these relative-unknowns, but you'd still lose your MIND with excitement if you had the chance to meet them in person.

While it's always easier, often more productive, and better for the ego to start with your friends and family and their existing connections, there's no reason you shouldn't also reach out to some of the less-easily-accessible humans.

The Big-Wonderfuls.

You might be able to find these women and men fairly easily online; on LinkedIn, on their personal websites, or on Twitter, for example.

Alternatively, if their contact details aren't easy to find, you might need to find someone who works with them and start there. An employee, a client, someone working for a business that connects with their business…

Reaching out to Big-Wonderfuls is something of an art form – one we teach in our Career Change Launch Pad – but that can also be developed through a little common sense and a little trial and error.

The most important things to remember are to be authentic, be respectful of their time and energy, and make your shared passion for what they're doing clear.

Big-Wonderfuls might feel a bit intimidating when you're considering doing your first few informational interviews, but you may well be surprised by how accommodating and supportive most people can be.

If you were to reach out for a Big-Wonderful, who might you start with?

Requesting the interview

Depending on how and where you've found your potential interviewee, you may be asking for an interview over the phone, via email, or in person.

Regardless of how you're making the approach, there are a few key principles to keep in mind.

Make them feel special

Of all the people you could reach out to, why are you approaching them for an interview?

On the surface, it might simply be because they know your Uncle Bob, but behind that there's something more.

They have a connection to an industry or field of work that inspires you, which means what they do for a living inspires you. You have a shared interest or passion – you are committed to the same things in life.

And they've done it – they're actively engaged in something that you're fascinated by.

They have something to teach you; they've achieved something you admire – and that's worthy of celebration.

Share with them why you're reaching out to them specifically, and celebrate what they're up to in the world.

Come from the heart

If you're considering a career change, you're likely facing some scary questions.

Is this really something you can do? What are the risks you're up against? What if it all goes wrong?

We're well-trained from an early age to approach all things 'career' with a veneer of cold professionalism, papering over cracks, contorting our vulnerabilities into strengths…

But if you really want to connect with someone and give them a reason to help you, it's best to be authentic about exactly where you're at.

What's driving you to reach out to people? What do you need to learn? What's at stake for you?

There's no need to turn your approach into a sob story, but being real about your request will connect on a human level with the person you're approaching, and give them a reason to make time for you.

Be specific

People who do interesting things are usually busy, and don't have time to try and deduce what you want from a round-the-houses, vague request.

How much time are you asking for? 30 minutes? An hour? (A personal request from me: please don't try to ask for 15 minutes of anyone's time – it takes that long to shake hands and sit down – it's simply not realistic.)

Not everyone has heard of the phrase 'informational interview', so explain what your intentions for the conversation are clearly.

You're not asking for a job, or for a foot in the door – you simply want to learn more about the work they do from someone who's already doing it, so you can be better informed as you work on your career change choices.

Make it easy

How can you make this as smooth and painless for them as possible?

Offer to meet them round the corner from their place of work.

Ask them to pick a time that suits them, and work around their schedule.

If it's easier, conduct the conversation over Skype.

Pay for the coffee.

Make this a pleasant, easy experience.

Before the interview

Do your homework

In the run-up to your meeting, take some time to get to know your interviewee.

Look them up on LinkedIn.

Check out their Twitter or their personal website.

If they write on an industry-related topic, read an article or two.

What projects have they been working on recently? What discussions do they get involved with online?

Knowing who you're talking to before you show up is vital.

It'll make your interviewee feel flattered and special – and relieved that they don't have to waste their time explaining the basics, telling you things you could have found out on your own.

Plus, it'll help you ask useful, interesting questions.

Questions like...

“I saw you worked on a pretty well-respected project quite early on in your career. How did you manage to do that without much previous experience?”

...are infinitely more useful to you (and fun for your interviewee to answer) than:

“What was your first job in this field?” or “So, what did you study?”

Prepare your Burning Three

Nobody enjoys that awkward pause in a conversation when you've both run out of things to say.

But it's equally weird to robotically work your way down a long list of pre-chosen questions, and miss out on the natural flow and unexpected insights of an organic discussion.

And if you're a natural chit-chatter, the 30 mins or the hour you've set aside for your conversation can easily disappear in a whirl of small-talk.

If you've managed to get this far, it would be a shame to walk away without the insights you were hoping for.

Be clear on the three burning questions you most want to get answers to, and note them down. With these at the front of your mind, you can chat and allow the dialogue to flow in whatever way feels natural, while knowing you're at least walking away with the fundamentals of what you need.

During the interview

Set the context

Even if you think you’ve been clear about the purpose of your conversation ahead of the meeting, your interviewee may still be unsure of what you're looking for from them.

Make it clear at the start of your chat what an informational interview is, why you're interested in speaking to them, and what you'd most like to walk away from the conversation having learned or achieved.

As Jackie discovered during her Launch Pad experience, sometimes people get the wrong end of the stick...

“I once contacted a woman who seemed very defensive and kept telling me that she didn't have any jobs to offer. Be clear in your own head what you want out of the interview, and communicate that to your interviewee.

“I found that some people thought you were hankering after a job, so it helped to be very clear at the beginning – to say, for example:

“'I wanted to talk to you today because I'm really interested in finding out about what you are doing in <insert industry here>.'” 
– Jackie (Launch Pad participant, June 2016)

Just taking a couple of minutes to set the stage can help put everyone at ease, and if your interviewee knows what you want to get out of the conversation, it's a lot easier for them to give it to you!

Start light

Remember: while this might be nerve-wracking for you, it could also be a new experience for your interviewee!

Be kind to them; ease into the conversation and make them feel comfortable with you.

A great way to do this, as one of our Launch Pad Alumni, David, points out, is to get them smiling early on.

“Start with questions about the positives: why they chose to work in this industry, why it's great, what parts of the role they love and why. I found this gave loads of opportunity for them to talk about themselves and open up, and it set me up with me lots of follow-on questions about the bits I was most interested in.

“Plus, later, that meant we were both relaxed enough to address the more challenging questions: if they had any regrets, or advice on what they would do differently if they had a chance to start over. It also created an opportunity to ask for other people I could talk to!”
– David (Launch Pad participant, June 2017)

Get real

A big reason to hold informational interviews is to find out the things you'd never normally get to hear about; and to get an idea of the reality of what a new career might look like.

Spend time celebrating and asking about the great elements of your interviewee's work, but remember to dig for the tough stuff, too. This is your opportunity to learn from the mistakes of others – don't let it slip by.

“For me, a good informational interview is all about specifics.

“I've found that people tend to gloss over the gritty bits and all the hard work that went into what made them successful, but these are the things I want to hear.

“It means I really have to listen, then pounce on a 'gap' and ask them to tell me more about that – a little like a job interview (but a lot nicer!).”
– Nina (Launch Pad participant, Feb 2016)

This rule goes both ways, too.

Don't try to 'impress' your interviewee or hide the fact that you're not yet an expert in the field you're talking about.

It's OK to be a beginner – and the more you embrace the curiosity and open mind of a beginner, the more you’ll learn.

Fears aside

It's easy to get nervous about informational interviews, especially when you're just starting out.

What will this person think of me? They must be busy – am I worth their time? What if I look silly?

If they've agreed to speak to you, then they're happy to have you there. And there's nothing more likely to kill the chemistry of a conversation than someone who's excessively nervous and apologetic.

Relax and enjoy the opportunity in front of you – and make sure you get what you came for.

“First step: deal with your feelings of guilt for 'wasting their time'.

“While it's not polite to drag it on forever, don't feel you have to blast through your questions.

“Also, don't get sucked into talking about your own career change to the detriment of finding out what you wanted to know about their industry....most people are fascinated by it!”
– John (Launch Pad participant, October 2016)

Be mindful

Show the person you're speaking to that you respect and appreciate their time.

If you've requested an hour to chat with them, keep an eye on the clock and let them know when you've got ten minutes left.

Chances are if the conversation is flowing, they'll be happy to keep chatting, but make sure they know they're not expected to stay beyond what you've agreed.

“I've had interviews where I asked for 30 minutes and we ended up chatting all afternoon – and others where we had to cut things off as soon as we hit the top of the hour.

“Even if things are going well, I always make a point of showing them that I don't take their time for granted.

“It's basic respect and although they often wave a hand dismissively and say they're happy to carry on, I know they appreciate it.”
– Melissa (Launch Pad participant, Feb 2016)

After the interview

Follow up

Say thank you as soon as you can!

Drop your interviewee an email, preferably on the same day, and let them know the one biggest thing you learned from the conversation.

People love to know that they've had a positive impact on someone – and they love to know how even more, so give them something specific to feel good about.

Maybe they shared something that relieved a concern you had about the field you're considering.

Perhaps they told you a story about their own experience that you were particularly inspired by.

Whatever they contributed to your thinking about your shift, acknowledge it specifically in your appreciation.

Follow up again

It might seem excessive, but try to give your interviewees an update on how things are going a month or two after your conversation.

And if you can tie their insights and contributions into your update, showing how they impacted your next steps, so much the better.

I've been interviewed by a number of career changers considering moving into my fields of interest, and I'm always over the moon to hear how they're getting on a couple of months down the road.

Not only does it feel good to be remembered, it also often jogs my memory and has me think of new ways I could help or support them.

Perhaps in the intervening months I've come across someone they might benefit from speaking to, or seen an article that could be of interest to them.

Seeing their name in my inbox can be exactly the catalyst I need to do what I wanted to do all along – support them further in their exploration of their new careers.

Share some love

Your interviewee gave you their time and insights – repay the favour by showing them you're thinking of them.

Stumble across an interesting article related to what they do online? Send them a link.

Meet someone they might be interested in speaking to? Reach out and ask if they'd like an introduction.

Done right, informational interviews are not just about you 'picking someone's brain' (even the phrase is gross – no wonder it makes you feel a bit slimy).

They're the beginning of a friendship – a relationship that could benefit both parties.

And, if you do decide to make further moves into their industry, by showing up as someone who consistently adds value, you'll be the first to spring to mind when opportunities arise.

Ultimately, 'informational interview' is just a fancy-sounding name for a useful conversation with someone interesting.

It's not a radical idea.

But if it's not already a core part of your career change process, it's time to get started.

There are very few other things you can do that are likely to move you faster and with less risk toward a career you love.

What can you do this week to get your first informational interview in the diary? Let me know in the comments below!

Natasha Stanley's picture

Natasha Stanley is Head Coach for Careershifters. She also speaks, writes and facilitates events on the art of human connection.