4 questions to ask yourself before you leave your current startup sales role.

I know the feeling…when hopelessness sets in as things start to sour at your startup. In those moments, when the world grows dark, it’s easy to want to abandon ship on the spot.


But sadly, I see so many sales people that jump too soon without truly understanding  what it was that caused the frustration in the first place. As a result, they end up stuck in a vicious cycle searching for that greener patch of grass: bouncing from one startup to the next and seeing the same problems at each without ever knowing why they can’t seem to find a gig that fits.


I’ve had that experience a few more times than I’d like to admit myself. But, I was also fortunate to break through at one point in my career and figure it out saving myself a lot of future angst.


Einstein said it best:


“The definition of insanity is doing the same thing over and over again and expecting a different result.”


So if you’re ready to bail, and this isn’t your first time on the merry-go-round (or even if it is), take a second to answer these 4 questions before you do to make sure you’re looking before you leap.

Question #1: What’s actually sucking the life out of me?


No, really. Get honest and specific here. Saying “bad leadership” or “a toxic environment” is not enough. Those are fluff answers, and if that’s all you’ve got, you’re bound to repeat the same mistake twice.


Here’s an example of what I mean from a comment one of my connections left on one of my LinkedIn postings (notice how specific she gets):


“In retrospect I should have looked more closely and compared the size of the ‘dream’ to the the company leadership’s (owners’) capabilities and characters. With lack of direction, financial knowledge, and professionalism, the company quickly turned into a sinister laboratory and the personnel into guinea pigs…and we all know what happens to guinea pigs in experiments…”


So what is it about your leadership or environment that is actually impacting you negatively? Is it a bad product/customer match that the leadership is not willing to iterate or change? Is it unrealistic goals? Are you so unbelievably micro-managed that you want to scream? Is it a lack of respect because said leader has zero experience in sales or your marketplace? Or is it a mismatch in dreams versus abilities like my comrade above?


The closer you can get to nailing down specifically what the problem is, the easier it will be to avoid repeating the same mistake again and finding a great gig in the future where you won’t face these problems.


It will also help you avoid leaving when you don’t need to. Because keep in mind, some of these things can be fixed if the leadership is willing to iterate.


Question #2: Are the reasons I want to leave things I can help fix?


I know you can’t fix a bad product, bad culture, or bad leadership directly. I’m not suggesting you must stick it out any of those situations.  


But I am saying, keep in mind that in sales you have to start all over when you make a move. It’s in your best interest to always remain part of the solution. If you have leadership that is willing to listen (or if you haven’t checked to see if they will), make sure you speak up before you bounce.


Not only could your situation improve, but if the changes you suggested are implemented and work, you’ll look like a genius.


For example, during a chat I had the head of sales at a young startup, he mentioned he had some legitimate worries regarding the long-term viability of his company’s current MRR. And not surprisingly, he was considering jumping ship.


But, I encouraged him to analyze their data and customer base a little more in depth before bailing. And tt turned out things weren’t all “doom and gloom” like he feared. We were able to pinpoint why the numbers were changing and how their customer base was evolving. And in actuality, their revenue quadrupled!


It was a terrific chance for him to grow as a leader and it also rejuvenated his perspective on the landscape for their business.


So when you think it’s the end, don’t jump before you’ve made every effort to try to fix the situation.


However, one thing to note: make sure you do it constructively. I know when emotions are running hot, you want nothing more than to flip the bird and slam the door behind you on your way out. So challenge yourself to remain helpful even in the heat of the moment.


Want help on how to this? Check out this awesome article on Lifehacker for more insight.



Question #3: Is my voice and opinion respected here or not?


If you’re always looking for ways to be a part of the solution, you’ll likely have a good feel for this already. But I want to put this question here because it’s very very important when it comes to determining whether you’re working in a place where you can succeed.


I probably don’t need to tell you how important a collaborative environment is (statistically, companies with engaged employees outperform the competition by 20%).


Here are a few questions you can use to analyze your current situation to see if it’s going to help you succeed:


  1. Is the feedback I’m receiving from my suggestions constructive or not?
  2. Have I seen the things I’m suggesting work in similar situations before?
  3. Are my suggestions reasonable?


Again, whether your voice is considered has a lot to do with how you’re using it. So make sure it’s constructive and helpful.


Question #4: Have I defined what my ideal next role should look like?


There’s an old saying: if you aim at nothing, you’ll hit it everytime.


This is especially true if you’re ready to make like a tree when it comes to your current sales startup gig. If you don’t know what you’re looking for…how are you going to find it?


My go to solution for finding a gig I love has been using a scorecard. This systematic approach takes the guesswork and emotion out of knowing if an opportunity is going to be one I love or not.


And, you can even use it to evaluate your current role to see if it’s actually a good fit for you.


I’ve written an entire post on using a scorecard to find your dream sales gig on Sales Hacker. I highly recommend you check it out if you’re already halfway out the door!

In summary…


The danger lies in making knee-jerk, emotional reactions without a tangible understanding of why you’re doing what you’re doing. Get systematic about defining what it is that’s making your life hell, and do a deep dive on the root cause.


If you do this, and find out you’re truly more of an order taker than a valued member of a team or your product/market/leadership mix isn’t jiving, I’d say it’s time to move on (as long as you know what your next step should look like).


Your turn: what other questions would you ask yourself before you leave your current startup role? Drop a note in the comments.


As always, thanks for reading!


Know someone who is ready to move on? Share this article with them.


-Amy Volas