When we started our prior company, I was a sales team of one. Then we were a team of two. Then a team of three. And so on. With my background in account management, I became our accidental sales leader.
What’s the first thing I did as accidental sales leader? Screw up a bunch of things, probably. But then I got myself some help. I am never afraid to chart new territory but I also value outside expertise!
I had the pleasure of working with five types of sales consultants as my team expanded and evolved. I’ll describe them in the order I engaged with them, because it speaks to what type of help I needed as the company grew and my experience level changed.
I hired her when we were just starting to get lift off. I was personally still doing almost all of the selling, with one employee helping. We didn’t have a team to speak off, just a couple of people who could get on the phone and talk to a prospect when I needed extra hands on deck. As a company we were doing well. It was time to grow the sales team, and I felt like I needed a coach. I was comfortable selling, and I was comfortable managing teams, but I had not combined those two skills before. I was entering uncharted territory.
I probably found The Generalist by typing “sales coach” in my search bar. She was local and had some good references. I can’t even recall if there were any set deliverables as part of our engagement. I paid her a small monthly retainer for about 3 months, and she:
- Had weekly calls with me (see below)
- Conducted a workshop at our office
My objective with the engagement was to make a plan to build the sales team. Her objective was different. She had me take a Myers-Briggs, and then wanted to talk about it. A lot. Over several long calls. I had never worked with a sales coach before so I went along with it. She also wanted me to have all my potential sales hires to take the Myers-Briggs as well, and to build my team based on the compatibility of our personalities. I found myself doing a lot of nodding and murmuring “uh huh”, thinking I would never do what she was suggesting. I was looking for ideas and action, not personality theories.
After a few weeks of dissecting me on the phone, she came in to our office to do a workshop. I thought it would be about how to sell, or something along those lines. The workshop ended up being about our messaging, our go to market strategy and our marketing programs. She wanted to lead us through exercises to define these things. But we already had that stuff in motion and it was going really well. She was treating our company as though it was pre-launch, pre-product and pre-market, but it wasn’t.
I tried to say open minded, but the engagement was brief. I don’t think it was a fail, as her business acumen was fantastic and I learned a few things about leading workshops. It just wasn’t what I wanted or needed at the time. I definitely didn’t feel any more prepared to rev up the company’s sales engine. I think this was a case of me buying an apple when I was looking for an orange.
I learned that is is important to be specific about what you are hoping to get out of a sales consultant, and to have the consultant outline their process and deliverables in advance. This helps make sure it’s a good fit. I just didn’t know what I didn’t know.
The Metrics-Driven Hard Ass
A couple of years later I hired the Metrics-Driven Hard-Ass. We had a few sales reps, and some SDRs. I had a pretty inexperienced sales manager running the team, and we were trying to understand what we needed to be doing in order to grow faster.
I remember spending a lot of my time wondering, “How are we doing?” and “How do I know if we are doing well or if we suck?” and “Is my team any good at this?”. And also, “Is my sales manager good at their job?”.
Because I had never been a sales leader before I had no relative benchmarks to draw on. I had no way of knowing if we were on the right track. We were selling. But were we selling enough? I didn’t know where to go next or what levers to pull on to drive the growth. We thought this consultant could look at our numbers, and our reps, and tell us how we were faring and what we needed to do better. That he could help us make a plan for more growth. He came highly recommended by one of my co-founders, who knew him personally.
His engagement, which lasted about three months total, was a one-time flat fee and for that we received:
- Inspection of the pipeline and historical numbers (to provide us insights on how we we were doing, in his opinion).
- Recommendations on metrics we should be tracking, and on changes to our opportunity stages to align with our sales process.
- Two on-site skill development workshops for our team.
- Several phone-based coaching sessions for my sales manager and myself.
- Shadowing a handful of calls to assess the skills of the individual reps.
He was so experienced, and so well respected in the sales community. But he didn’t have any answers about our relative performance either. He couldn’t look at our numbers and tell us if they were good enough. Numbers are relative and so many variables can impact them. That was my biggest lesson and it was worth the entire engagement to have learned it! I needed it at the time—his lack of insight into how well we were doing helped me stop doubting myself. I just wish he had told me that before we hired him.
He looked at our numbers and made a formula that said if we do X then we will sell Y. He wanted everyone to be making 100 dials a day. Period. He didn’t care about anything else—skills, culture, product/market fit, quality of leads, ability of the reps. Nothing. He just built a formula based on every rep making 100 calls a day, getting X number of appointments, which would yield Y number of opportunities which would yield Z number of new customers. He created this formula based on our benchmarks.
In this regard, I learned the value of your own benchmarks and using them to plot what you can achieve based on various levers. Until then I was just throwing goals agains the wall, “let’s close 100 customers this year” without really understanding if it were possible and how we would do it.
The Hard-Ass also led two fantastic workshops for our team. He covered how to get the first appointment, and how to get a yes at every step in the funnel. He transferred tons of knowledge to the team and inspired them to push harder. These were valuable sessions. But, we didn’t record the workshops, and my sales manager didn’t reinforce the content and learnings, so within weeks the team was using his techniques less and less frequently (even though they worked!).
Teaching a team new tricks isn’t just about telling them. I learned that for a workshop to be valuable the concepts need to be reinforced and rewarded until they take root. Otherwise, the investment of money and time to conduct the workshop is entirely wasted.
Ultimately, the Metric-Driven Hard Ass wasn’t a great fit for us culturally and we wound down his engagement. He made us miserable with his militaristic attitudes about dials per day. His relentless focus on 100 calls a day, to the exclusion of every other lever we could be pulling, was too narrow for us. I wanted to work on skills like getting more appointments from the same dials, getting better appointments and closing deals. He wanted me to scale the sales team based solely on the math of his 100 calls a day formula.
The Bull in the China Shop
Several years later, we were again at an inflection point. Having not run the sales team myself directly for awhile, I found myself without a sales manager (yet another bad fit), and about 15 direct reports. Our team was comprised of account executives (AEs) and sales development reps (SDRs). I was a bit overwhelmed thinking about how to get my arms around this team and lead them forward, especially because we wanted to double our new contract value in the coming year.
I didn’t want yet another sales manager, I wanted success. I decided to run the team myself. I wanted to create a strong, sustainable sales culture and was over the rollercoaster of trying to do that with a manager under me who was running the team.
I turned to a sales consultant who I was familiar with via his blogging content. I had briefly hired him about a year before, to coach my then sales manager.
I knew his style. He was brash. He was in your face. He was also extremely knowledgable about sales leadership. I was ready to really embrace my role as sales leader and knew he had a ton of knowledge that would help me.
I worked with him for about a year and his engagement included:
- Monthly visits to our office; during the visits we would review reps sales plans, do pipeline reviews and coaching.
- Quarterly extended visits with me to review our benchmarks and performance, determine comp plans and hiring targets, etc
- Screening potential new sales reps, as part of our hiring process.
- Shadowing sales calls to help assess rep skills and provide one on one coaching.
- A revamp of our our reporting and processes to help us scale.
I really learned how to be a sales manager from the Bull-in-a-China-Shop coach. He taught me the fundamentals and processes for running a sales team.
He didn’t help me create a culture, but he pointed out that I didn’t have one. He didn’t help me set up my coaching cadence, but he pointed out I didn’t have one. He didn’t help me recruit great people, but he taught me a repeatable process for doing so. He didn’t help me assess the skills of my reps, but he showed me how critical its was to do so in a consistent, quantifiable manner.
He pointed a lot of things out to me that I needed shoved in my face. I learned so much from him. His style was not mine however, and the culture he wanted to create wasn’t my vision. It took me about a year to realize that everything he said and did wasn’t the gospel, and that I was empowered to take what I wanted from him and leave the rest.
We were really running the team together. But he was an antagonizer. He was in everyone’s face holding them radically accountable for being professionals and being good at their job. That was awesome, because up until then we didn’t have a strong culture of accountability. But many people found it off putting. He rubbed most of the team the wrong way. His very presence manufactured tension. Intense tension. My alliance with him alienated some of my team who found him too aggressive and too direct.
That’s his style and he fully owns it. And I needed it at the time. I just should have asked him to back off when I knew he was about to go too far. I forgot sometimes that I was the client and I could have an opinion too. But at the end of the day, I learned the fundamentals of sales leadership from him and because of that I created my own way of hold reps accountable to hit their numbers and my own sales management style.
I often say that everything I learned about sales management I learned from him. It’s a bit of an overstatement, because I had a lot of on the job training, but in essence it’s true.
The Keynote Speaker
Our team was established and we were off to the races. I had my culture, my cadence, my metrics and a great group of AEs and SDRs. Every quarter we got together for a planning meeting (an artifact from the bull in the china shop era), and I wanted to surprise the team with an outside speaker. As a department we had just finished a book that we all loved, so I hired the author to come in for a full-day workshop. His workshop deliverables included:
- Prep calls with me, and some of our sales people, to understand our environment.
- A full-day on-site session including a 2-hour keynote and then workshop type sessions.
- A post-event debrief call with me.
This was a high-impact day. He shared a lot of wisdom and inspiration, and did it in a very approachable, relatable way. He took the content of his book and expanded it with real-world role play, and if/then discussions. I learned that having an external speaker can be incredibly valuable, both for teaching and inspiring a team. We gobbled up his content and committed to putting it into practice after the workshop. Again, we probably didn’t do enough reinforcement of the content. Although we put it into practice, and it was helpful, but I can’t say it made its way firmly into our culture. Three months after the workshop I don’t think I could point to permanent techniques we had adopted other than some ad hoc tips & tricks.
Investments in outside consultants and speakers need to turned into action for you to receive the maximum value. That requires a commitment of sales leadership to continue to socialize and adopt the content long after the speaker has left the building.
I came away from this engagement thinking it was a big win. I loved the day we spent with the keynote speaker and everyone agreed we got a lot of value from it.
I hired The Blogger at a time when our sales team was well established. We had our s&!t together. We were selling, we were growing, we were firing on all cylinders. And I had such a good experience a year earlier with the Keynote Speaker, I was ready to do it again.
As a team, we focused a lot on skill development and reinforcement. In our discussions, there was always this one blogger we kept talking about. We read everything he published each week, and we always learned something new, or got fresh perspective that helped us improve our skills. We referenced his blog constantly. His content was so compelling, and he was so respected by the team, I decided to reach out to him to see if he could do a workshop and coaching for our reps. Our engagement included:
- A full-day workshop, video taped so that new team members could access the content.
- A sample of a playbook he had done for another client of his and the promise to create one for us (it never materialized although we asked about it several times).
- A post-workshop webinar to answer any questions the rep had about the new skills they had learned and to see how his lessons were working for the team in the real world.
So, this was an interesting engagement. We really felt like The Blogger walked on water and had a lot of valuable content to impart to the team. But the truth is, his workshop covered the exact content of his blog, and we were all so deeply familiar with his blog that there wasn’t a whole lot of “ah-ha” moments or new material that took our learning deeper.
But he was so smooth, and I thought we would get so much out of the relationship because he was going to take his content and mold into a very specific deal playbook for us that was unique to our business. That was part of his deliverables. But…it literally never materialized. He promised it a couple of times, we asked for it a couple of times, and then we dropped it and moved on, feeling like the entire engagement was just sort of zero-impact. We didn’t learn anything. But, we did keep reading his blog, and I do love his content!
In retrospect, that playbook deliverable was important to me, and I should have held him accountable for delivering it. I also should have asked for samples of other workshops or references, because it is possible that I could have learned ahead of time that his in-person content was no higher impact than his online written content.
All in all, I am so grateful for all of the experiences I had with the 5 sales consultants. I hope this helps you decide what type of sales consultant is right for you, and what to expect out of the engagement. Of course, results will vary—so much of what happens between a consultant and an organization is chemistry, timing and culture. Your experience and outcomes with these very same consultants could be radically different. This is just one point (ok, five points) on the curve of many.
For any sales consultant to be effective, the most important thing is for sales leadership to sustain what is learned. If you hire a keynote speaker, it’s a moment in time and it’s basically gone as soon as the keynote is over unless you reinforce the concepts of the keynote throughout the year. If you hire someone for an engagement, have them set you up for success and then don’t work the program and plan you put in place, it was a pointless effort. Pull the best from whatever sales consultant or speaker you hire, and then find a way to sustainably work that into your sales culture and rep development. Good luck!