Challenges between small to mid to enterprise companies


This week, I was talking with some of my team. For context, we are a small-ish, boutique, consulting firm that targets global enterprise clients. It’s a heck of a dichotomy. I was talking about the persona we should be hiring for our team as we are in a rapid growth stage.

I have a personal sense that the type of person that is good at introducing agility to an old stalwart of Enterprise process needs to have a unique skill set of credibility, grit, and familiarity with the bureaucracy that infects most large companies.

By contrast, I would position startups to have much less restriction on process, so the balance tips towards credibility and energy in that space.

Since this conversation, I have been reflecting on what I said and am challanging if I was correct in my line of thinking. I am curious what others sense about the correlation of organization size to skills that maximize success in that context.


As a person that has worked in agile transformations in large companies (global 50) and startups (~200 employees), I agree with you. I find my career path turning more closely towards the startup environments as that is where I can dive in and make “shit happen” fast. The challenge of ripping down red tape is a fight I’ve grown tired of in large companies. Also, I find startups are more in a “do or die” situation and their appetite for improvement is high, and their tolerance for continued failure (status quo) is low. There is no protection of a bottomless vault of money paid for by other successful areas of a small business. If I can’t coach well in a startup, I’ll know fast (and get fired). In an enterprise, you can spend months banging your head on the wall talking people through things before you know whether or not you are actually succeeding. In a startup, you have to land fast, deliver faster, and be quite willing to get your hands dirty and lead by example (my personal preference)! That’s my experience at least.

Also, if anyone knows of any good startups (under 200 employees) in need of a coach (or blended SM, PO, etc), please let me know as I have a good candidate looking for a new opportunity in the Philly area!


You might find a single individual able to do both. But probably easier to find one that prefers enterprise consulting and one that prefers startups.

I for one would prefer coaching the willing and not fighting lethargy.


I think I mostly agree with the needed attributes you’ve mentioned. I’d add one to the ‘large company’ side though, and that would be patience. It would be an interesting attribute to screen for as part of the hiring process, but it’s critical. The arch of change is longer.


I could argure the willing reside in both at the team level.


I think you can take your cue from the neuroscience of relatability with influence. Your potential client is making an immediate assessment is this person like me or are they a threat? People who have left corporate because they have been frustrated can be good candidates - they have ability to blend in, speak the language but now have a service offering (eg via your company) to do something different. They didn’t have that when in the corporate. So yes — familiarity is very important. Equally, a graceful contempt for the old ways of doing thing and a willingness to do what needs doing to make the changes…

Now that I have said this, I wonder if the attribute you want t hire for is emotional intelligence and flexibility. Observant enough to see what flies in the company and adapt language behaviours to suit… and here’s the kicker, still be personally authentic :smiley:


+1 to “People who have left corporate because they have been frustrated can be good candidates - they have ability to blend in, speak the language but now have a service offering (eg via your company) to do something different.”

Ryan, you know that in 2017 I went looking for a Fortune 500 in Atlanta to be a part of for Agile/DevOps transformation work – and there are 16 or so such companies to choose from – in order to be an Intrapreneurial Disruptor. It had been 20 years since I was in the Fortune 500 space as an employee, and 10 since I had one as a client. There are other crazies like me out there who have the mix, but I would do as Jen suggested and look for ex-Pats.