7 Sales Leadership Mistakes That Cost My Team Millions of Dollars

I've ran small teams of three up to 110 plus employees doing multiple nine figures in new business sales each year and I've won tons of awards like presence Club but I've also made a ton of mistakes in sales leadership that have easily cost me and my company's tens of millions of dollars today I'm going to share with you seven of my biggest leadership mistakes that caused my sales team to fail so you can avoid them as a founder or sales team leader mistake number one not hiring the right profile now when I first started when

I was hiring people I didn't have a real process in place ultimately if I felt pretty good about our conversation I'm like oh I probably should hire them that was definitely a huge mistake for example there was a guy obviously not going to say their name but I had a great rapport with them he did a great job answering the cookie cutter questions that was provided for me and I like Jive really well with him on top of that we had this indirect connection where I knew his cousin from school so I just felt like

this is just like a match made in heaven and I brought them on board after I brought them on board I was really excited and pretty quickly I found out I had made a mistake their background didn't align they didn't really have the level experience I needed they didn't have the skills and hate to say it even their values didn't really align as well and because of that ultimately fast forward a few months later and they didn't end up working out and I basically wasted their time in my time and it cost me easily millions

of dollars in that time frame from the cost of a lost deal to hiring to them replace them cuz now I Wast another 3 to 6 months looking for somebody new now fortunately I've learned from making mistakes like this and I hate to say I made it only one time but I made it multiple times but really the self is quite simple it is to get really crystal clear on exactly who the hiring profile you're looking for and being really clear on exactly what criteria that they have in place that you want to vet out

before you bring them on board and there must be a good reason behind it some things to think about as well their past job experience what type of results they've received so far their miss the actual value system they have to how they fit in with the rest of the team as well so you want to be clear and have a hiring profile or score card that you can align an interview to ensure they match a certain profile way it just increases your chances of success if you decide to bring them on board now one

quick side note I also realize that mistake I made early on is also what's known as the halo effect meaning you pull one attribute from the background and you put almost a halo over over them and everything else is a pink flag a red flag you completely avoid now I've done that because I known his past background so you ought to be really aware that even when you're build out your profile to be really clear on those specific criteria you want to have but ensure none of them is creating a halo effect so for example

the mistake I see some SAS leaders make is they say I want to hire people who only have SAS experience but the reality is just because they have sass experience doesn't mean they'll be a great rep for example if you are a startup software founder with a small sales team and you may think it's a great idea to hire someone who has worked at huge companies like say Salesforce just because they work at Salesforce doesn't mean they'll be great at your company because when they work for a larger organization they may have different tools resources

Etc in place to help them be more successful versus you may need someone who maybe is grittier who can adapt on the Fly who can wear multiple hats and it's not to say people at sales forces can't do that but you want to hire people who have the right values and right skills that allow line to what you're actually hiring for so don't have a halo effect for things like a past background experience or even if they worked at certain companies CU that may bias your actual decision and doesn't always mean it's directly correlated or

causes the right type of results you're going to get from hiring that type of person so once you kneel down the hiring profile and you're starting to hire the right people don't make mistake number two like I did which was have really poor and terrible onboarding now when I started onboarding for all the past companies was hey just watch what I'm doing and do that or hey follow this other rep around and just do what they're basically doing that was my onboarding and I thought that's a how suppos to onboard people and for some people

they can figure it out by doing that on the hob results it might take a little longer but they can eventually figure it out and that's great but generally speaking for most people they need clear Direction and support and I didn't realize that until my first couple hires got brought in and I basically threw them in the deep end and they were completely lost didn't know where to go and I basically blamed them instead taking full ownership on myself which meant I had a bad process so the solve is quite simple which is have really

clear expectations and map out of clear onboarding so I went from providing completely zero direction to completely transition to a 90-day onboarding where each day and each week was clearly mapped out on exactly what the new hire was going to do what were the objectives what were the outcomes so they knew what they would learn as a result this way they could see walking in okay this boss of mine has a plan and is invest sit in my success versus on the opposite side I'm sure those first few hires feel like I probably didn't care

about them at all by thr in the deep end so provide that 90-day training or longer to ensure they are set up for Success this offic can provide training the classroom in field work on sales call doing the actual work it there different things going to help increase their skills and speed up their ramp time as fast as possible the really cool part is once I started doing this I also implemented a really tight feedback loop in which they would provide me a weekly just report of what happened the week and what they learn and

any questions they had this now G me a really tight feedback to improve their skills and help guide and Coach them because now they can see what they learn they can see what they're developing and also since they're involved in the process their speed to success drastically went up over time I find it to get better and better and I found by continually improving the onboarding process the Reps would be happier more engaged the first 12 months survival rate went up drastically and they got results faster and they were happier and I was happier too

It ultimately saved me money in the long term I still be more prepared and set them up for a success with company mistake number three I didn't provide a consistent sales system so I didn't realize as I was bringing new people on everyone had a different background some people were very much relationship sellers some were very transactional some were hard closers some had strategic sales someone had work with inbound leads etc etc ET you get my point they all have just a very background of experiences not immediately I eventually realized is most of them didn't

really have a system or process in place they just did whatever the company have put in place for them whether that was good or bad some there bad habits some had process some had no process at all and the truth was most of them if you just ask them how are they successful they'd have really generic answers like oh I worked really hard or my customer just really liked me and that's not repeatable as a sales system and what I found was ultimately everyone because of their background and the levels of experience they had they

all had a different way of explaining sales and our sales system so it was inconsistent across the board of what we did as a team which made it hard to coach train develop to get everyone on the same page so this took me a while to figure out but once I figured this out and I realized this that's when I started to train on a consistent sales system for everyone a certain way that we prospected a certain way we wrote emails spoke on the phones handle objections to how we Rite discoveries to demos Etc and

I'm not saying a a system where they had to mimic it perfectly but there were Frameworks that we would all fall along so we had the same language same terminology we look at the same things we work to improve the same parts of the process so we were all on the same page which allowed us to rise up together as a team and the really cool part was because now we had a framework to base it off of we knew we use it to diagnose and actually improve areas of a sales process for example if

you're on a road trip and you have Google Maps to to map out where you are to where you want to go if you know the path to get there if you go off course by looking the map you know how to get back on course and that's what a sales system really was for our sales team this allowed repeat ability and scalability and I'll give you a really simple example I remember taking over team in 2012 because I had already learned my mistakes from this situation here I built a sales system for my team

so I started training them on the system on what I was doing before get them all on the same page so that we has common language and bond but on top of that new hires as they came in I put them through the same system it was also a little bit easier cuz they're new follow what I was are going to do and that was really powerful and it got to the point where after another year or two passing we kept producing these top performers other leaders were send reps to my team because they knew

when reps went through my system they came out of rockar so it became a very consistent and scalable system because we train on process and framework which is scalable versus each rep doing whatever they want to do and being all over the place because when you have the Frameworks in place and then each rep can add on their own Flavor now it's becomes the next level because at least the Baseline is the same for everyone else mistake number four that I was making inconsistent ongoing training now after someone went through onboarding and even when I

got to the point where 90 days I thought I was basically done with training with them I'm like oh they got they figured it out they should know everything to know they'll never forget they're going to be awesome amazing little bit go and crush it and boy was I wrong it was it's like a pro basketball team that's training the pre-season and then when the season starts the coach is like all right we're not going to practice good luck see you at the games that's basically what how was doing it's pretty silly when you kind

of think of it that way so as I realized and really just internalize that training should be an ongoing thing and coaching should be an ongoing thing I started Implement a weekly train where we're role playing the fundamentals making sure they're on lockdown role play the toughest situations role playing specific challenges we're facing the marketplace role playing anything that I knew take my my team to to the next level and ultim because of that they got better and better over time and they had that repetition that was going to be really off the field in

practice with me together and when they saw each other kind of rise up as a team it was amazing cuz they could help train to help each other as a result but it was up to me as a leader to create that environment having an ongoing consistent training and this is even for the top reps to the bottom reps because ultimately they all become better at their game they want to keep their skills sharp and then we the way we do it is we train as a team what happened as a result of that they

got better every single week they closed more deals they produced better results it was just a win-win win across the board mistake number five not coaching live calls now early on I was really really worried about being perceived as a micromanager so I was pretty much hands off you know bringing them in I'm training a little bit I'm like all right cool go do your thing go crush it I'd even tend live sales calls with him but I wouldn't jump in to help I wouldn't really give much feedback after I just say good job keep

doing what you're doing and I thought that was me being a good leader being a good coach but then I realized I was actually hindering them I wasn't actually helping them what was the point of me even being on those calls so what did I do I started coaching them after the calls I would review with them how the call went I'd share three things I did an incredible job with and review three things to really focus on that to make the biggest imp impact on their calls and if we had multiple calls that day

the really cool part was I would see them start to apply those learnings to the next call and if we had multiple calls I could see it start improve each time and that became really powerful because now they had a really tight feedback loop and what I realized was the Reps crave feedback they wanted to do well they were already working their tals off to be in that meeting they definitely wanted to go as well as possible actually move the deal forward versus just ROM meeting so fortunately it's a very simple saw but I started

consistently every single week I was in the field with reps 3 to 4 days full sales calls with them seeing what's going on Coach them you know after coaching them before taking over parts to show them how to do certain things as well so this way they can see it live in the field things we discussed in theory in the actual calls now to actually improve and the really beautiful part about today's time is if you're running virtual calls you can listen to call recording as well so if you can't be on there live you

can you can do call recordings that's what I do with my team it's amazing for coaching and guiding them help them become more successful cuz ultimately your number one job as a leader is to make your team successful and when they are successful you are more successful mistake number six not measuring the right metrics early on I was taught to look at very simple metrics such as number deals and total revenue but the issue is that only tells you one part of the story it doesn't tell you how efficient a rep or team actually is

I realized there are no leading indicators so things that are going to predict future success and only lagging indicators which are metrics that show past results that you can't change anyways and I personally start to measure things such as number of coold calls connect rate booking rate show up rate close rate and more this gave me a better picture of how good how efficient a rep actually is so for example I had taken over a team in 2012 and won the Reps on my team in this first half of the quarter he is number one

out of 50 plus reps so on paper most Revenue most deals closed he looked like a rock star and if I would just base it off this data point I'm like cool he's good I don't need to help him at all see you later keep doing what you're doing but the reality is is when you know it to look at multiple metrics to make a good decision based off what's at hand you start to see different pictures so for example I started looking at his data and I took a look at almost 90% of the

revenue deals he had closed that part of the quarter so far was because of the territory he took over was my old territory that I just got promoted out of and there were all these deals which they already ready to go he just had to go pick up pick up signatures and that was really it no real work and the other amounts of DLC Clos was a very insignificant amount in fact if you actually out all the volume that was just basically gifted to him he was actually the very bottom of the 50 plus reps

that were getting ranked in that same report when you look at other metrics like effici metric like a closing ratio it was less than 10% so there's a lot of opportunity there now this doesn't mean measure all the possible metrics out there the key is being really clear what metrics actually matter the most and make sure you measure them accordingly and for me personally these ones I found have worked really well for me and m i me in the past was I only picked the ones I was being told when there's other are far more

important because if I only base my decisions based off the me they told me to look at that could set me up in a bad position down the rad when I suddenly realize the rep is actually not that good or team is not that good and they need far more help mistake number seven that I was making not providing ongoing support coaching and accountability you can hire right on board right train right measure right and still fail as a leader if you don't provide the proper coaching support and accountability for every single rep on your

team early on I was far too Loosey Goosey and just thought that reps would just come to me when they needed help and some of them did for sure and that was definitely great but for others they may have realize that but they didn't come to me whether they were scared to didn't know they had to or frankly just weren't thinking about it and thought things were just going okay and I remember when I realized this this is my first quarter as a brand new sales leader in which I was trying to be the cool

boss be their friend try not to like be just in in their business and I remember this first quarter after I made all these other mistakes after the quarter wrapped up and we completely missed our number and I asked my team what do you think happened and they were just kind of surprised like oh I guess it just happened I just had no idea the quarter flew by I'm working hard and I realized that wasn't their fault that was my fault as the leader I didn't s with the right system I provide proper coaching support

and accountability and for them to be surprised 13 weeks later that they miss their number that falls on me as a leader to solve that problem so I made a very simple shift we we already had our weekly sales meet we already had a training as well and I started to do weekly one of- ons with each rep and it was really simple it wasn't anything crazy it wasn't a pipeline review I just sit down with them I check in with them see how they were doing what was going on in their world what are

they struggling with walk through their numbers so they knew exactly where they stood and cover the variance between where they stood and where they wanted to go and put together a game plan for the upcoming week to help move them closer towards their goals and the goals we're talking about here was not just hitting the quota but they were their own personal goals for examp example if they had a personal goal if they wanted to make you know $225,000 in commission for the quarter and the reason is because they wanted the commission to send their

kids to private school we'd walk them towards where they were currently and well as a variance to help them pay for the tuition for the kids private school so every week we did that and what happen was really really amazing is we uncover obstacles to work through challenges to work through they felt supported on top of that it was a space for them to share anything was on their mind right wrong or indifferent so this we can work together to help them overcome it and they can run through the rest of the week with support

from me as well what really surprised me was a lot of them appreciate the accountability because the accountability was why didn't you do this and Grilling them it was just holding them accountable to where they wanted to go and then help me provide the tools the resources the coach support to help them get there and this game their one-onone time with me I'll separate from the rest of the team so this way they continue to thot cuz ultimately nobody wakes up and says I want to suck at my job today they all woke up they

want to do a good job they want to perform and they know if their boss has their back and their saler has their back they're going to be much happier they they'll Thrive and show more discretion your effort as a result so there you have it seven sales leadership mics that have literally cost me tens of millions of dollars from my sales teams I hope you learn from my mistakes and hope you can avoid some of my mistakes and now if you want to learn how to build a top 1% sales te in less than

90 days I'll see you in the next video right here