Hiccups in Sales Leadership: Embracing Oopsies and Building back Confidence!

Hiccups in Sales Leadership: Embracing Oopsies and Building back Confidence!

Oct 05, 2023

My daughter thinks she has superpowers - she makes us call her Sky Pup (IYKYK). She's four and has all the confidence in the world. She's fearless - until she isn't and starts to second guess herself.


I'd imagine if we skipped forward some 30-40 years she will still be doing the same. Sales Leadership often is faced with second guessing their confidence after flubs and oopsies. Here are a few ways these hiccups may be showing up:


The Rollercoaster of Numbers:


Remember riding a rollercoaster? It goes up and down - your stomach drops or maybe you lose your lunch upon exit. That's what looking at team numbers can feel like! One minute you're celebrating with your team and the next you are wondering if Salesforce is having a moment because there is no way the pipeline could look this grim.


Fun fact, your pipeline may look even more grim than you are led to believe. Why? We are finding more and more companies who have a loosey/goosey approach to pipeline management. For anyone who is Type A, this can be a confidence buster as more and more deals push for no reason and forecasting becomes a nightmare and you start to circling the disaster drain.


Quick Pep Talk: Your team is where they are right now. That doesn't mean things can't change. It may seem monumental to you to change a process or the way you have done business, but once you identify just how big the gap is - it makes it easier to change course. Take some deep breathes - dive into what is truly going on and swallow your pride. You will build confidence knowing you interjected early vs. letting it all fester into a mess (re: you losing your job).


The "Fake It 'Til You Make It" Act:


Many of us in Sales Leadership resemble this. Faking it until we figure it out - all the while digging our team into a deeper hole because we are too proud to ask for help! We fake the confidence piece as it relates to our skill set so that no one will call us out.


It's totally normal to feel the sales leadership jitters - it is not beneficial to hide it and think that you "know everything" and can fix it yourself if there is a clear skills gap. This may show up as a sales leader or team with no sales coaching in place (because the sales leader is faking this skill) and with a full pipeline, this critical step for coaching and development being missed because the team is "crushing it".

Big oops.


Quick Pep Talk: You are not alone. Not every sales leader knows everything there is to know about running a sales organization. Just like every pro started out as a rookie in any sports organization. There is a learning curve. Swallow your pride and find someone on the team who is adept in the areas where you falter and ask for them to spearhead a new project. You used to be able to Ask Geeves - but literally you can google anything to get a baseline until you face it enough times and bridge that skills gap.


More Discounts Than The Dollar Store


The team is coming at you left and right with discounts and you are signing off on them to get the sale. This lack of confidence is shining through in that your team is sinking and slinging deals at all costs in order hit numbers. Is this sustainable or a sign of something deeper going on? It is up to you as the Sales Leader to recognize this trend and intervene with a strategy. Yikes! That could mean that you aren't liked and whoa - what a blow to your confidence (more on that here).


Hubspot notes that offering a sales discount projects a lack of confidence. In some cases, a sales discount can come off as you telling your customers, "We don't believe in our product or service enough to sell it at full price."


Quick Pep Talk: Do I know the problems we solve for? Does my team know the problems we solve for? If the answer is no to either of these, no wonder the team is discounting to race to a number. Take a step back, root yourself and your team in the problems you solve. Take those discount oops in stride and move past it with a solid strategy of problem identification.


Remember, confidence comes from developing new skills and learning from time in the seat. We fail ourselves and our teams when we pretend to know it all and let our oopsies and hiccups go unnoticed. Nothing like reaching out for help to ignite a little confidence boost!


If your team is struggling in any of the areas mentioned above, shoot me a message and let's chat.