(despite what companies try to tell you)

We marketers are often accused of making a living talking out of our butts. Slick veneer, little substance.

That’s not entirely an unjustified claim, it pains me to say.

Not only do we gloss up our communication to customers and each other, but we also do it when we describe our own company and its culture through the recruiting process.

I think we’re collectively starting to resign ourselves to the reality that posted job descriptions and About Us details are filled with rather templated and perfunctory language. As a result, when we apply for a job, we are still quite conscious of the work that lies ahead to understand what the role truly is and what it’s like to work for the company. This wide knowledge gap must be closed before we accept an offer, should we be fortunate enough to receive one.

The fact that we characterize our roles and cultures with little or insufficient insight is a function of a number of issues that collide when recruiting. Among them:

  • Recruiting is ‘extra’ work added to our busy schedule, so we default to templated language to just get the posting out there
  • Our minds subconsciously gravitate to aspirational models of what we want our culture to be, perhaps also thinking this one hire will help us take a giant step toward getting there
  • We actually do not have a firm grasp our own culture…or have at least taken the time to understand it to a deep enough level that we can communicate it to others

Not surprisingly, organizations continue to look for new (better!) thinking with each hire. We understandably would rather not just replace someone, but instead upgrade our net workforce as a result of recruiting efforts. To that end, we champion our preference for innovative thinkers who thrive in our entrepreneurial culture…..



That word appears in the majority of culture self-descriptions, and for good reason – it initially draws us in. But sooner than later, it takes on the stank of a throwaway adjective when we search for evidence of this claim and become anxious or even frustrated as we come up empty. Many of us are in fact innovative and want to stretch the limits of our thinking and abilities. A culture that is genuinely entrepreneurial can drive a ton of our career satisfaction, while one that is not can suck the vitality out of our work day. It matters.

I am here to tell you that yes, this is all-to-often a throwaway adjective, influenced by the factors I laid out above. Many cultures – perhaps most – are in fact not all that entrepreneurial; and so, we have a problem. The game as a job seeker, then, is to not be baited…and I’m here to help.

If you ask an interviewer why their company is entrepreneurial, they will likely wax philosophic about how they value people who ‘think outside of the box’. (::cringe:: or ::eyeroll:: — take your pick). Our thought bubble wonders which companies are not in fact looking for such things and so we don’t feel like this company has separated itself or closed in on the truth.

Want to dig deeper into a culture to figure out if it is in fact entrepreneurial? Look for these signals:

They are actually working on new stuff.

…and we have to consider carefully what ‘new’ means. The more entrepreneurial the company is, the more it develops completely new business models. From scratch. Leveraging some but not a lot of existing company assets. That means, new products, new customers and completely new infrastructures to commercialize and support the product or service.

Entrepreneurship is not a phenomenon unique to the startup domain. Alphabet is a massive corporation that grows through intrapreneurship as much as through existing businesses. Driverless cars would be a prime example.

To understand how entrepreneurial a company is, I like to ask one of the executive how they expect to be making most of their money in 5 years. Assuming you get more than just spitting and sputtering in return, consider how ‘new’ the thinking is.

For smaller and medium-sized companies especially, the notion of being ‘entrepreneurial’ can be much more relaxed once your first product is built. It involves a consistent drive to break new ground. New marketing, new markets, an active pipeline to materially improve and develop the core product all count.

Processes, systems & resources to incubate new thinking.

Successful intrapreneurship is something of a systemic nature and less the byproduct of chiding subordinates to think out of the box more frequently. I worked for the consumer products arm of Johnson & Johnson a dozen years ago. Our particular operating company isolated some play money annually to incubate new thinking. Yes, in this big ol’ corporation there was this mini eco-system of entrepreneurship — a cross-functional exec team of about ten who held a quarterly forum where scrubs like me could pitch ideas and gain real support.

Marketing/new product peeps like me got to stand up in front of this collegial crowd (I remember two execs whispering to each other about how cool my shoes were during one of my pitches) and talk about an opportunity. We got playfully booed for every PowerPoint slide we put up, because *we* were to be the pitch, not the slides. This was not a place to be all corporate-y. We talked at length about our consumers and how to solve problems. Primary filters were applied. If it sounded good we got some cash out of the play fund to take the next step, which was usually more formal market research or resources to create a prototype.

I also recently met a change consultant who installs online innovation platforms in big companies. It all starts with an evolved version of a chat and message board system where ideas can be incubated on the fly during the work day. The company (execs) then intervenes in the platform to take the more promising idea threads to the next level in an offline environment. The bonus is you have an awesome tool for employee engagement that allows literally everyone to innovate in-the-moment, with little effort, on their own time, and as a result of their own passion. 7-7-7!

A lot of good comes out of these approaches. Processes are a great thing to layer over innovation because it gives your awesome thinking a place to go.

A history of innovation and leadership.

You can neutralize any rhetoric by looking at the track record. Many insights to be gleaned by understanding a) what a company considers as innovation, b) how the innovation came into being and c) how consistently a puch for innovation manifests itself in the marketplace. Gives you a good sense of where they are along with the likelihood for sustainability of innovation practice.

Prudent risk-taking.

A few years ago I wrote a post on the Barriers to Real Innovation. You can test for some of those. If I’m talking to my future direct boss or CEO I like to probe on how they react to and evaluate an idea that I’d bring to them if it was something they have never seen before either in the company or the marketplace itself. Hint: if they are all caught up in ROI metrics and are looking for empirical guarantees, they don’t have the right mindset. If they can integrate strong nose for consumer need and marketplace opportunity with analytical filters, you’ve got something.

The role of failure.

Ask how failure is viewed: is it an essential process for learning and progress or is it heavily penalized…? Look for examples of failures that have not stalled a career or have delivered essential silver linings.


This is huge. In times when I have been particularly ballsy in interviews I have actually asked about the biggest decision I could make without upward authorization (or the biggest one my interviewer could make) when told about the company’s entrepreneurial culture. Proceed with caution on this one because, you may quickly suck the air out of an otherwise constructive interview as the interviewer spits and sputters trying to answer you. They usually can’t. And then they get some form of embarrassed or annoyed for not being able to back up their BS. So, best to maybe just ask openly how the company empowers people, if they think that’s important part of culture.

Freedom and flexibility.

This is really empowerment in all aspects of your work that are not major decision points.

How much of your work day is your own? Or, are you caught in meetings all day being told what to think about and when…and otherwise sorting out the chaos?

Is there work-life flexibility? Do people work from home or more fertile remote locations and at any hour of the day? Is face time important? Most will say ‘no’ so then you have to ask for examples of high performers who are not perpetually present. Again, tread carefully.


And when you are in fact corralled into projects or meetings, is there an agile mindset? Do you work in small teams? Are meetings run efficiently? Is there a track record of adjourning gatherings in under an hour?

And one I love to probe on – do systems handle all the mundane tasks to aid quick decision making or do employees have to compensate for the lack of data infrastructure? I have had jobs where even at a senior level I felt like I was pulling data all day when I wished I could just query what I needed from any device so I could just get on with it. Soul crushing, I tell you.

If YOU spend your time being decision support more than taking action you’re in trouble. That’s most big companies, so be careful. I have blogged endlessly about this issue, which is near the top of my list of why most companies have yet to reach the 21st century in how they operate.

Results orientation and reward systems.

Great entrepreneurial companies should be careful about seeing mistakes as fatal if there was sensible rationale behind taking the risk (big ‘if’ but there you go). But the crazy good thinking is also stimulated by reward that is both monetary and non-monetary. In great companies you are compensated handsomely for incubating new business models (in the startup world you get a cut of the financial success, so there’s your benchmark). At the very least, intrapreneurship is the path to create completely new career avenues that may or may not go with upward mobility. So that’s what you’re looking for – a ‘what’s in it for me’ end point for all the creativity, passion and work you invest.


Notice how I didn’t focus on specific questions for you to ask of others. In this post I simply offered characteristics of entrepreneurial companies while I encourage you to embark on a journey to uncover as many as you can…or at least until you feel the company is a great landing place for you and your innovative spirit.

I try not to give templates and formulas for these sorts of things. The main reason is the amount of judgment that is required to be an effective marketer or leader.  Here I have helped you understand what to look for, but it’s up to you to assess when, how and to whom you direct your questions or statements. As I suggested earlier, probing into these issues is a constructive process for you in your job search, but can simultaneously result in uncomfortable or even offensive moments as you stumble upon unsettling truths, in the case where you’re outing a company that can’t walk the talk.

One tip that might help is that if you get to the very end of the interview process and maybe even have an offer in hand, you end up having more leverage to ask questions. The tide shifts a bit as the company now tries to please you to close the deal. That’s your opening to press a bit in those final meetings or calls to facilitate your decision. What I do in advance of a meeting is share my agenda and objectives, hoping my transparency is well-received and allows for preparation of a clear story on the company’s side. So you can probe a bit as you go but if you handle it well, you can dial up your questions when you have an ear.

One final point…and I’ll make it to interviewing companies although it applies to candidates as well. Don’t lose sight of the end game, which is to find great candidates…and keep them. That’s more likely to happen if there’s a two-way fit. To get there, take the time to showcase your company for all that it is, with accuracy and authenticity. Candidates will appreciate it and you’re saving yourself the trouble of not having to backfill the role again in six months once your new hire realizes they have been duped. Not only are you incurring senseless expense of resources, but in the interim you have an unmotivated butt in the seat.

In such a case, everyone loses. Take it upon yourself to not let that happen.