A successful career, in my view, comes from three things: talent,

good luck, and good decision-making.

Let's assume you're talented, and let's assume luck is out of your hands.

The lever that you're left with is your decision-making.

How can you make the strongest decisions possible, whether you're

recruiting or looking to get recruited?

Hello, and welcome to The Get.

I'm your host, Erica Seidel.

I spend my days recruiting CMOs and VPs of Marketing in B2B SaaS.

My tagline is I place the make-money marketing leaders,

not the make-it-pretty ones.

With my role, I have a front-row seat to the trends, tribulations, and triumphs of

today's top marketing leaders in B2B SaaS.

And now with The Get you do, too.

The Get is designed to drive smart decisions around recruiting and

leadership in B2B SaaS marketing.

This season, we focus on the race to reduce risk.

When it comes to a match between a company and a CMO, how can you

find out what you need to find out before saying yes so that you make

a match that sticks and flourishes?

Today, you'll hear from me on flaws in decision-making to

avoid in the recruiting process.

Then, you'll hear more perspectives from my guest, Melissa Sargeant,

who has been a CMO multiple times.

The first part of making a good decision is realizing that

there's a decision to be made.

Sometimes it doesn't feel like it, but with many things around

careers and hiring we do most often have more choice than we think.

The second part is having a good process for decision-making.

As we have seen with other episodes, it's important to have some framework,

some key things that you examine intentionally before saying yes.

And the third part is avoiding getting tripped up with your decision-making.

In my executive search role, I have seen people fall into a bunch of

different decision-making traps.

Let's review some of these, and as I go through these, consider

which ones you have fallen prey to.

The first is trusting someone else's due diligence without doing your own.

Like when you're hiring a marketing leader, and you trust a reference

from someone you know who has worked with the person before so much so

that you skip your own due diligence.

It can also happen when you're a CMO candidate and you already

know the CEO or CFO or CRO.

You think, "That person is there.

They did their research and they're smart and we click.

So it is likely a great fit for me."

You scrutinize the match less than you would otherwise.

A second flaw in decision-making is thinking that the company

has a greater appetite for transformation than it actually does.

Every CMO needs to navigate what I call the Peacemaker/Changemaker Paradox.

They have to thread that needle between making change and doing so in

a way that brings the company along.

Sometimes, the company is just not ready for the change that someone can bring.

Another flaw - underestimating the amount of stretch in the role, thinking

that the new marketing leader will be as coachable as they need to be or that

the CEO has the capacity or ability to upskill the new head of marketing.

The next flaw is representative bias, thinking that this

situation is so much like another.

Oh, it's the same size company, the same investors, so the same

playbook I used then will work now.

Or the same person who did this in another company will succeed here.

These factors can be good indicators, but they don't necessarily predict success.

Another flaw is commitment bias.

I put so much into this, so I should continue.

It's like continuing to wait for a bus that isn't coming.

Staying in a role for too long once it is clear it is just not

a fit, is an example of this.

Or, investing a lot of time into a recruiting process and

wanting it to just be over.

So you say yes even when there are big reservations.

The next flaw is confirmation bias, looking for information to

support our initial impression.

For example, you have great interviews with someone.

You feel a good vibe, but you haven't really seen the person in action, and

you haven't tapped into things like behavioral assessments to vet the match.

Another flaw - falling in love with the product instead of the product market fit.

Or thinking that because you know the ICP or you are the ICP, it'll be easy.

The last flaw that comes to mind is falling in love with the

company that someone worked at.

Like, yay, I'm going to get to work with the person who led marketing at company

X, Y, Z, rather than focusing on how they approach their role and their work style.

Remember, sometimes a company is successful because of somebody's

contribution in marketing, and sometimes it is successful

despite their contribution.

If you are just as fascinated by decision science as me, there are

lots of great resources on it.

There's a fabulous book I recommend to many clients and candidates.

It's called Decisive by Chip and Dan Heath.

Check it out if you are facing a big career or life decision.

Now, let's bring on my guest, Melissa Sargeant.

Melissa has been CMO four times, most recently at AlphaSense and previously

at Litmus, SugarCRM, and ChannelAdvisor.

Before that, she was in senior marketing roles at Avalara and CA.

She has driven great scale-up journeys in her career, and I'm

really impressed by her sheer range as a leader and as a marketer.

She knows a lot about decision-making in recruiting, both hiring and getting hired.

So Melissa, welcome to The Get.

I'm glad to have you here.

Thank you so very much.

I'm really excited to be here.

Thanks for the invitation.

So you have been a CMO four times now, and I'm wondering if you can look back

to your, your previous self, you know, before you started your CMO journey.

What do you know now that you didn't know before your first CMO gig?

As it relates to reducing risk in the recruiting process,

which is our theme here.

I think the main thing that I didn't understand was that I needed to map out in

that first role as I was interviewing for it, the things that were important to me.

So, for example, for some people, as a CMO, it might be really important to

report into the CEO so that you can have a strategic seat at that table and really

be there as part of the executive team.

It might also be important, very important to really understand things like product

market fit because we get that, you know, the most glowy, best pictures of

what's going on from the product side of the house as we're interviewing.

And I wish I had, I still would've made the same decision I made, but now I

know that there's this list of these immutable things that I will not negotiate

upon that are critical to my success in the role, critical to the success

of the team, and being able to recruit people to that organization once I get

there and that I have to stick to that and not let someone kind of talk me

out of some things that are important.

Really, because it's ultimately gonna drive the success in that role and

the outcomes you're able to drive.

That's fascinating.

So have you ever had somebody try to talk you out of something where your gut was

saying, "Oh no, I'm gonna stick with me."

And then, you know, you're kind of like trying to see the logic

of what they were saying, but also your gut was saying something else?

Yes, and specifically as it relates to product market fit.

It was an organization that had grown really quickly, had product market

fit, and then as it happens in the market, things are always changing.

The only constant we can manage is change, and product market fit started to slip.

And so it was very clear to me that that was happening.

And so when I brought it up during the interview process, they tried to convince

me, no, it's really just a pipeline issue.

And I said, I agree that you have a pipeline issue, but the pipeline issue

is related to product market fit.

And I can come in and help you work through the product market fit issues,

but we all have to be intellectually honest together that that's the core

issue here, and we can work through that.

And then, over time, that's gonna help us from a pipeline perspective.

But if we don't have a shared understanding of what the real

issue is, in six months, they're not gonna be happy with me.

In six months, I'm not gonna be happy with them.

And, and no one really moves the needle forward.

Yeah, it's a great point because product market fit, sometimes companies are

like, you either have it or you don't.

But it seems like you have it mostly but never perfectly.

And then it changes, and you know, like maybe you had it a few months

ago but things have changed.

And now you need to find a new, just a new place to sit with product market fit.

Yeah, it, it's definitely not one and done.

It's, you know, it's something that's continually evolving and you have

to really keep that top of mind.

Yeah, yeah.

So can you double click here on, maybe share a couple of things,

one or two things that you have done before saying yes to a job?

Something you have asked in particular, or information you found out that

others could learn from as they are looking to mitigate their risk?

Definitely.

One thing is as we go through these processes, and it may sound familiar to

people, you go into these interviews, whether it's the first one or you're,

you know, in your fifth or sixth round, and they'll map out the plan for you.

Say, here's the agenda.

I'm gonna talk about some things that the interviewer's gonna share some things.

Then, they're gonna ask some questions, and I'm gonna leave you, candidate,

five to ten minutes at the end of this to answer any questions that you have.

And I think that that's common at the beginning of the process

because you're trying to figure out synergies, does this make sense?

But as a candidate, you need much, much more time to be able to figure out if

this is the right opportunity for you.

And so what I have done when I find myself in those situations, and if I'm continuing

to advance through the process, is I will put together my list of questions, and

whenever that next interview is coming up, particularly if it's gonna be my manager,

the CEO, I will write out the questions.

I will send it forty-eight hours in advance of the interview and say, I know

you probably have some agenda items that you wanna talk through with me, but here

are a list of questions to help guide our discussion and things that I'm really

interested in going further in with you.

And if we're not able to get to it in this next discussion, I would like

to make a request that we schedule a follow-up discussion so we can

both get through these questions.

My view is that a good manager, a good hiring manager, should be

excited that the person has been thoughtful about this and wants to

go through this process with them.

I really like that.

I actually had a client once who, her approach for interviewing, she was a

CMO who was hiring people on her team, and her approach to interviewing was,

the first conversation was all about her answering questions that the candidate

had, and the second conversation was her actually interviewing the person.

Because she felt like once they were smarter about the business, they

would be smarter about the interview.

It was a bigger investment on her time, you know, on her part, but these

were vetted candidates beforehand.

I'm wondering, can you share maybe a question or two that a CEO

has reacted really strongly to?

That you've done in your forty-eight hours before or during the interview?

So the areas I really like to dig deep into are the dynamics around how

that executive team works together.

I will usually start at a higher level and ask about how does

strategy get developed here?

And often people will say something like, we do OKRs, or we do the V2MOM framework.

Great.

I love frameworks.

How do you get there?

What happens before that comes on paper?

Oh, we go on an offsite.

Fantastic.

What does that offsite look like?

Do you, Ms.

CEO, come to that meeting with documentation that you've put

together in terms of your goals and here's how you see the strategy?

Do you have each of your executive team members come prepared with, you

know, a presentation or a talk track on what they see the strategy is?

How does that happen?

It's very telling about the dynamics of that organization because what I've seen

is some very top-down structures where the CEO, or maybe it's a founder CEO,

is, you know, very common, certainly in my space, has a, is the visionary in the

company and they're the ones, they're the person that's looking around corners.

So they have a very clear view of what they think that strategy should be.

Or perhaps it's a more mature organization and all the key stakeholders, all the

key executives come with what they think.

They've done their research and they've gotten their feedback from customers

and they come to the table with that.

How that process happens and the discussions that happen around it

is incredible insight on how that team works together on a daily

basis and what you can expect to see in your executive team meetings.

Because in those meetings, my view is that everyone should be talking.

And some organizations, if you see or if you hear, it seems like there's one person

who talks the most and others are just listening and maybe asking a question.

That's something you want to understand a bit more about because if everybody really

has a strategic seat at that table, how that process happens is really critical.

The part two of that that I will ask them is, how do you disagree?

You get lots of different responses to that.

In a healthy working environment, there is a level of disagreement that's

necessary to move the company forward.

It can be done in a respectful and professional way, but it should be a red

flag for candidates if they see those interactions, and if you feel like you

get into these spirited discussions and then you go away from that meeting, and

if you have to spend the next two weeks repairing your relationship with your

colleagues, it's probably not a healthy organization that celebrates and wants

those diverse voices at the table.

So for me, I really wanna understand how do we work together?

And that can be a challenging question for them to answer because

there's so many facets to that.

One of the examples I typically bring up is say, okay, how do you disagree?

Like what happens when you're on very different sides.

Do you go through this debating process and as the CEO you're listening to

this and then you make the decision and you have a contract and how

you're gonna interact with each other and it's, we disagree and commit?

What does that look like for your organization?

If they haven't thought that through, that's something that, you

know, you need to be aware of as a candidate going into that situation.

If they have a real, like, yes, we absolutely disagree and commit and

that's how we're gonna interact with each other on a regular basis.

So fascinating.

Follow up question, are you looking for the kind of structure of decision-making

and, and fighting to be set before you walk in and then you kind of inherit that?

Or are you looking for a situation where you, as a CMO, are going to

influence that if it's not totally bait?

You know, 'cause those are two different ways of reacting.

You know, the inheriting it versus kind of promulgating it.

It's a little bit of both in that I want to understand how they

operate today so I can think through how I'm gonna best engage with

them as a group and individually.

If the company's just not at that place, and I work at a lot of, have worked

at a lot of earlier stage companies or high-growth companies where you're

growing so fast you don't always have time to figure out all this management

stuff that underpins the business.

I wanna be able to have a voice and have a discussion around these things.

And there's lots of training and books and things that we can do as

leaders to get better at it because, ultimately, that's a key part of our job.

The rest of the organization trusts us to get this strategy right.

They trust us to work together as productive partners so that they

can take that cue from us and go and do the execution elements

that ladder up to that strategy.

Right.

Right.

Makes sense.

I love those questions.

It's so, because I feel like with those two questions about how is strategy

set and how do you disagree, you could just ask those two and that could

be like two hours of conversation right there and a ton of learning.

So, that's great.

Let's talk about flaws in decision-making.

I'd love for you to share your perspective, both on the side

of having gotten recruited and having recruited teams before.

Can you talk about maybe some, you know, top flaws in decision-making

that you've seen or that you think people should be most wary of?

And maybe it's something that you've, you know, kind of done battle with yourself.

Curious to hear your take there.

I will start from the latter part of that because I've made several

mistakes in this process over the years.

I think it's, it's trusting your gut.

Your gut is your truth.

And one of the words I think that is overused a bit today,

but I'll say it, red flags.

When you see something and you're like, that just doesn't quite feel

right, or I don't understand that.

For me, I know that because I'm a tech geek, I will tend to overlook

these, you know, red flags.

And I've had certain situations where they weren't red flags.

I would say it was like this beacon of light with sparkles

and fireworks saying, "Melissa!

Danger, Melissa!

Danger, Melissa!"

And I will have overlooked it because I would be enamored with

some other part of the organization, or I really liked the team and, you

know, I would second guess myself.

I'm, I'm being too critical here.

Now, I'm incredibly intentional about that, that if I see a red

flag, and I know it's a red flag because I feel it in my gut.

Something doesn't feel right.

And that's where your truth is.

And I think that's true for both if you're interviewing candidates and

something comes up and it doesn't quite feel right around that, or if you are the

person that's interviewing for the role.

And the way I manage that, personally, is I will remind myself, and sometimes

I even put a sticky note on my display that says, "Stay curious."

And for me that means keep asking questions.

Get a little more curiosity.

Get more clarity.

See if there's something that you're misunderstanding there or

there's some information that you don't have around that red flag.

But if you can't get it and you still have that feeling, you have to honor it.

And that can be really, really hard.

If it's, you know, a company that you're super excited about.

We're in a time now where it's really competitive for roles

and you're excited about that.

But every time, whether it was a role that I chose or a candidate that I

was hiring, and that red flag, that twinge I get in my stomach was ignored,

I paid for it every single time.

Yeah.

Yeah.

You know, I have a coach who told me once something really smart.

She said, "Your gut doesn't speak English."

So I love how you're talking about kind of interrogating your gut, right?

It's like the gut has to have the space to say its truth, and you have to realize

that it's talking, and then you have to realize it's not talking in English,

or whatever language you, you speak.

And then it's, oh, let me try to translate for it and with it and

interrogate it to, uh, to figure out what it's trying to tell me.

That just stuck with me so, so much.

And I like what you're saying.

It's almost like when you get married, you know, it's like, oh, there's this

little thing, but are you okay with that little thing becoming like a really

big thing, potentially, over time?

[Chuckling] Exactly.

Because - right - because what's a small little, you know, gut

question mark initially becomes a bigger question mark over time.

Yeah.

Well said.

So it sounds like for you, you know, the flaw in decision-making

is just not trusting the gut and, and not following the feelings.

Are there any others that you've seen, in particular, you know, show

up when hiring or getting hired?

So a lot of times we'll get candidates whom have been recommended to us by

people with whom we've worked in the past, or maybe they're at the company.

And that's always great because, you know, in general, I think great

people tend to attract great people.

We still have to go through the same process with them and not necessarily

give them an advantage in that scenario.

Because if they were great in some other organization with that person

- every organization is different.

Every culture is gonna be different.

How organizations make decisions, how people engage with each other, the culture

on that team could be quite different.

It doesn't necessarily translate into success in that next role.

It's great to get that feedback and it's a place for you to ask lots

of questions and learn more, but I intentionally, now, again, it's

a mistake I've made in the past.

I don't start when I'm looking at a slate of candidates automatically adding

points to that person because, oh, they know this person and I love that person.

I would work with them a hundred times, and if they say they're perfect for

this, then you know, I trust them.

They might, I'm sure that person is fantastic.

It just doesn't mean that that's automatically gonna translate into

the role that you're recruiting for.

Or for you as a candidate that you're going into that the same

thing is gonna be true for you.

Yeah, yeah.

Well said.

Thank you for sharing.

I'd love to also get your take, for people who are new in a CMO role, they

often come into an organization that's kind of skeptical about marketing.

So do you have any tips for once somebody has gotten the job, and assuming it's the

right job, how do they turn the company from being skeptical about marketing

to being supportive about marketing?

Trust is built through transparency.

And a lot of CMOs come into organizations - I joke that,

why do they always hire us last?

I feel like in every role it's like, "We got everything else in order, Melissa.

Now, can you just come and like, you know, you've got that magic dust

that you carry around with you and sprinkle it over here and in 90 days,

you know, everything will be better."

Sometimes CMO roles are really revenue rescue missions for companies.

And so the way to set expectations around that is to be super transparent.

And we talk a lot about 30-60-90.

When I come into an organization, there's a couple of things I do regardless.

First, I tell everybody, including my boss, don't ask me to make a

decision in the first thirty days.

The answer is no.

I'm not making any decisions.

I don't care how on fire you believe this to be.

It's been on fire for a while.

It can burn a little bit longer.

And then that thirty days is a listening tour on steroids, you know,

from every single person on my team.

I do a start, stop, continue with every single person in the marketing

organization, and then I schedule a one-on-one with them and talk through it.

I spent all the time with my peers on the executive team, as well as

their first line managers, and then I set up calls, same calls, listening

tours with customers, if partners are a part of your business, if you're

a channel business, I wanna talk to your top five channel partners.

And I am just listening and asking questions and really being

present in that first thirty days.

From there, I come back and share with everyone, here's what I heard, here's what

I learned, here's what I think about that, and here are my next three to five steps.

So it's really leaning into that, you know, 30-60-90, but I'm coming

in because it's the only time, those first thirty days are my only

opportunity to be completely objective.

We all get sucked into it, no matter how great we are at our

craft, and I spend lots of time with customers and partners so that I get

that real world voice in my head.

But the, the not knowing and not having biases is really, really important.

And the only way to really understand, for me, is to not say much except

for to ask a lot of questions and really think through it.

Setting yourself up when you start with people to let them know,

this is what I'm going to do.

So when you see me in a meeting, just asking questions, and I'm

not saying, well, why don't you do this and why don't you do that?

That's a hundred percent intentional.

So don't think it's because I'm disengaged or, you know, I'm listening so that

I can come back to you in a really thoughtful way with the information

I need to make good recommendations and good decisions on the next steps.

The trick to all this is the transparency and making sure your manager, if it's

a CEO, whomever that is, understands this is what I'm going to do, this

is the approach I'm gonna take, and here are the checkpoints you're

gonna get along the way from me.

You know, I believe trust comes from transparency, and as marketers, we

are great at marketing companies, products, launches, you name it.

Give us an ice cream cone and we will sell the truck.

Ask us to market ourselves or explain ourselves and what we're trying to do,

and it's challenging for all of us.

So be really explicit and super transparent of what you're doing, why

you're doing this, and what they can expect, and then follow through on it.

And then when you have those checkpoint meetings, remind them.

Remember when I said that I was gonna, you know, go on this listening tour?

Well, I did.

Here are the people I talked to.

And one of the tricks in marketing, I think for this transparency,

and I joke with my teams all the time that 'cause they'll say,

but we already told them that.

Hmm, if you told 'em ten times, you should have told 'em fifteen.

You have to repeat yourself over and over and over.

But that trust comes over time with the transparency and them understanding

the decisions you're making, why you're making them, where their input

is showing up in these decisions so that they felt heard and continue

that and make that part of your operating rhythm as a marketing leader.

I love that.

It reminds me of the whole, tell 'em what you're gonna tell him, tell them,

and then tell 'em what you told them, and just applying that to, to marketing.

And I like that inhabiting that kind of hyper objective period for the

first month on the, on the role.

That's great.

Thank you for sharing.

I have one final question for you.

This is something I ask almost everybody that comes on the show, and

that is what is your favorite question that you like to ask when you are

interviewing somebody for your team?

So the very first question I ask, and I believe marketers, regardless

of where you are in the marketing organization, marketers are storytellers.

And the first question I ask people is, tell me your story.

And there's a hint - if somebody just plays back their resume to me?

Ehh, that's not your story.

That's not who you are.

Tell me your story and go back as far as you want.

Start with your kindergarten teacher.

I would love to hear, you know, what Ms.

Smith taught you in kindergarten and how that influenced your life.

Because I wanna hear how they shaped that story and the easiest way to get

people to relax and really show you who they are is to tell their story

of how they got to who they are today.

And that's where we start the discussion from.

That's cool.

Do you give them bounds?

Like, okay, I want you to take no more than five minutes to do this?

Because I mean, somebody could go on and on and on and half an hour goes by, right?

Right.

I will say like, you know, don't take more than ten minutes.

'Cause I might interrupt and say, oh wait, say a little bit more about that.

That was really interesting.

When did you decide that, you know, you were gonna work at a wildlife rescue?

Like, tell me more about that.

What drove you to make that decision?

Where were you in your life?

You, as you know, as a leader, curiosity, integrity, and empathy - that's who I am.

And so for me to be effective, I really need to know a

little bit about that person.

Or a lot if they want to, to share that with me.

But having that frame of reference about every single person on your team will

really change the way you think about working with them, about the stretch

projects that you might give them, how to best give them feedback, how to cue

in when they're maybe not having such a good time, but they're too shy to

say anything, and you can be proactive.

It is your entryway to really start to know that person.

And everybody wants to be known and understood.

Yeah.

That's great.

Yeah, I had a, a former boss who used to say, "Everybody has a sign on their

chest saying, 'Make me feel special.'" And I think when people tell their story,

you know, it's like they feel special.

And they also let their guard down a little bit?

So you can kind of see the things that are gonna come out that wouldn't come

out when they're practicing a recorded, you know, rehearsed answer to a question.

Yes.

Yeah, awesome.

Well, thank you so much for joining the show, Melissa.

This has been great chatting with you.

And true to form, we covered a lot of, a lot of things, a lot of range here.

So, thank you, again.

Thank you so much for having me.

I really appreciate it.

It was great talking to you.

You too.

That was Melissa Sargeant.

Now, think about what flaws in decision-making or red flags that you

need to be most aware of and what's most important for you to look out

for in your next recruiting decision.

Next time on The Get, you'll hear more from me and from another guest.

Don't miss it.

Thanks for listening to The Get.

I'm your host, Erica Seidel.

The Get is here to drive smart decisions around recruiting and

leadership in B2B SaaS marketing.

We explore the trends, tribulations, and triumphs of today's top

marketing leaders in B2B SaaS.

If you liked this episode, please share it.

For more about The Get, visit TheGetPodcast.com.

To learn more about my executive search practice, which focuses on recruiting the

make-money marketing leaders rather than the make-it-pretty ones, follow me on

LinkedIn or visit theconnectivegood.com.

The Get is produced by Evo Terra of Simpler Media Productions.