Deciding on the next step in your professional journey is never easy, especially when you are a top performer eyeing a leadership position. In this episode, Mark Cox and Dave Hanley discuss sales career advancement, offering a roadmap for high-performing salespeople who are contemplating a transition into management. Beyond the promotion, they explore the complexities of internal sales approvals and the delicate balance between managing existing accounts and driving new business. Listen in as they provide tactical advice on building a sales playbook, prioritizing your time effectively, and ensuring you have the right support before making the leap into a leadership role.
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Office Hours- episode4 - Cracking The Code On Sales Career Advancement
Dave, welcome back to the show. Thanks for driving this. We're in Friday casual attire.
It’s good to see you. It's a short week here in the US. I get the joy of celebrating both Canada Day and Independence Day here.
A Canadian in the US. I notice you enjoy celebrating all holidays.
I try. It's important.
Lots of different nationalities. Multicountries. You're on the Tim Ferriss one-day workweek.
I'm trying.
Dave, what do we have?
Transitioning From Top Salesperson To Effective Sales Manager
We got some good ones. The first one in particular is something that is always a tough one. I'm keen to hear your thoughts on this, and we can talk through it. Question one is from Sharon. Sharon says, “I'm currently the most senior salesperson in a small but growing company. The CEO has approached me about moving into a sales manager role, but I'm not quite sure whether I want this opportunity or not. I enjoy my day-to-day, but I am curious whether this is the natural next step for me. How should I think about this opportunity?”
Sharon, what a great question. We can take our time on this one. You're in a great position to weigh in on this as well. Sharon, there are probably three ways to look at this when this opportunity presents itself. First, you're looking at it from your perspective. What do you want to do? The second thing would be looking at it from the company perspective. What are they going to do for you? The third might be looking at it from the team's perspective as well.
There are three different ways of looking at it. As always, you've got to start with the why. It's nice that the opportunity presented itself. The first question for you, Sharon, is what do you want to do with your career? When you think of what you're doing and what you're enjoying in your lifestyle, only you can answer that question.
What are your career goals and aspirations? What are you looking to do? Are you looking to stay in sales? Do you want to go into management? Are you looking to continue to be ambitious, grow in business, and do other roles and senior management roles outside of sales? Starting there, Sharon, is probably a good starting point, first and foremost. What are you looking to do with your career?
There are a lot of people that we coach and a lot of people that come into our workshops that are career salespeople. They realized early on in their career that they wanted to be direct contributors. They love working with clients. They love autonomy, and frankly, they love mastery. It’s easier to be a direct contributor salesperson, be good at it, and continue to be the Wayne Gretzky of the hockey team when you're playing. It's far more difficult to be the coach of that team.
Sales Career Advancement: It’s easier to be a direct contributor salesperson, be good at it, and continue to be the Wayne Gretzky of the hockey team when you're playing. It's far more difficult to be the coach of that team.
The other thing I’d take a look at, Sharon, as well, particularly because you said it was a small business, and we're a small business, is to take a look and ask yourself how long you have been doing your role. Do you understand sales enough before jumping into management? This is the first filter for all of these things. What's right for you?
One of the things we see very frequently is that because of the growth of the SaaS industry, and it exploded over the last couple of years, a lot of it was outside money coming in. That money had to be spent on sales and marketing teams. That's what the boards wanted to see. They grew too quickly. Those companies did very well, but for the most part, it was order-taking.
What would happen is somebody became an SDR for eight months, then they're managing a team of SDRs, and then they become an outside sales rep. They made every leap too quickly. As long as they were selling for Salesforce or HubSpot in 2016, it was order-taking. They might change industries. They got to a senior management position. They hadn't developed the skills along every stage of the process to be able to compete in a market that might not be growing, where you have to steal market share from somebody else. These are things to think of for you, Sharon.
The second thing that I think about is what's the company going to do for Sharon? Commonly, entrepreneurial companies are the same way. In The Funnel is an entrepreneurial company. Frankly, we're trying to get out of that. We pull a lot from the people who work with us. What Sharon needs to ask is, is the company going to provide any management training, or is she going to stop being a salesperson on a Friday, and on Monday, she's managing the team? Where is the training that's going to help elevate her skillset when she jumps to this next level?
What's the onboarding plan? Oftentimes, the Friday promotion and on Monday, I'm doing the role, what's the expectation? Are we going to give her a reasonable ramp-up to get good at this new job the same way we would give a new salesperson? Does she have 90 days before we're squeezing her to make sure the whole team is hitting their numbers? She's going to be pretty unhappy quickly, and that'll convert into her making the team unhappy pretty quickly. What do you think? Do some of these things resonate with you?
I seem to remember an excerpt from your book. You told the story about going from being the best salesperson on the team to the worst manager on the team. Companies need to be wary of that problem, taking your best salesperson and going, “You're the best salesperson. Let's make you the manager.” Not only did you lose your best salesperson all of a sudden, but you gained a manager that's not very effective.
It is a different skillset. I've seen a lot of people struggle with that transition where they go from getting their hands dirty every day, rolling up their sleeves, and doing deals to having to sit in a room with underperforming salespeople, coach them, and resist the urge to say, “Do this. Here's how you do this.” You have to sit back and say, “I need to coach this person to develop them and make them better.” As opposed to being tactical. You have to be a lot more strategic.
It's so much harder. Then, it is understanding why you want to do that. That was the thing for me. This is a long time ago, but the first time I made the leap, it felt a little late to me. I’d always thought, “I'm going up the ranks. I want to be the CEO of a large corporation. I want to get to senior executive levels at a minimum, so I've got to get going.” I never took the pause and said, “Why do I want to do that? Is it money?” Frankly, if it was money doing certain things, I could have made a lot more money continuing to be a direct contributor.
It's not uncommon for the top salespeople in the company to be making more than the actual sales leader. I've seen that several times.
Frequently. First of all, that comes into play. The second thing is I hadn't reconciled in my own mind that leadership was about developing other people. In my mind, I was still thinking leadership is making me look bigger and better. This is the Friday-to-Monday problem, where everybody on that team is arms and legs helping me get my quota. That's the real job. My quota is eight times larger than it was on Friday. That's the issue.
In fact, looking back, I was a better coach, in that particular instance, to the other seven people on the sales team. I was a better coach to them when I was a peer because I could be balanced and calm. I listened well. I didn't feel any pressure. When they were asking me what to do and how to do it and were looking for coaching, I could give them reasonable feedback. I had a lot of time for them. I enjoyed them. I liked sharing that way.
As soon as I got put into management, with me, there was no ramp-up time. A week later, I'm forecasting for the whole team. I'm looking at them, saying, “You're not getting the job done, and I'm not happy.” Since I didn't know what to do, I defaulted to telling them what to do. Nobody wants to be told what to do.
The Entrepreneur’s Dilemma: When To Hire A Sales Leader
Let's look at this one from the flip side. We have a lot of people who tune in to this show who are entrepreneurs, business owners, or CEOs, and they're running sales. What's the alternative here for them? I know it's not the easiest thing to do where you have a sales team with 3, 4, or 5 people, and you go, “Everyone's doing great. Now, I need some leadership.” Can you bring in somebody from the outside to become that sales leader? That also is a sticky situation. All of a sudden, the salespeople are like, “What's going on here? Why don't you promote one of us?” What does that look like? How do you do that effectively?
First of all, so many of our clients are entrepreneurs. I have a lot of love for entrepreneurs. There is certainly a very specific profile to a successful entrepreneur. There's almost a similar profile at every level. An entrepreneur getting a business from $0 to $5 million, one getting from $5 million to $15 million, one getting from $15 million to $50 million. There are these profiles of entrepreneurs.
My coaching to people tuning in would be that if you've got a sales team under 6 or 7, and you're an entrepreneur. You've got a product in the marketplace and revenue, and you're profitable. I'm sorry to say this, but you have to run the sales team. There are a number of reasons for that. First of all, you need to run the sales organization so that we can figure out how to scale this thing and capture what was in your brain and the way you were able to convince a client, and how you articulated your value proposition, and how you intuitively knew the ideal client profile.
If you're an entrepreneur, you have to run the sales team so that we can figure out how to scale and capture what was in your brain.
We've got to communicate those things to the first team of up to 6 or 7 salespeople. It's important for the entrepreneur to do that because they also start to have empathy for what the sales team is going through. It's going to get them in front of more clients and see it from the salesperson's perspective. They need to get to a point where they have a definitive sales playbook for the business. Meaning, we can articulate and share the value prop. We prioritize the target market. We have a demand generation program. We understand our sales process. We understand sales strategy.
When you get to that point, and you've run the team, and you have a playbook, that's when I'd go away and hire somebody else. You’re like, “Now, I need to get the team to fourteen people or I might need two sales leaders.” That's when I bring somebody else in. If I do it too soon and I try to absolve myself of that ownership and accountability, the new sales leader coming in to manage four people has to go to the owner-operator-entrepreneur so often anyway that it's like the owner-entrepreneur needs to run it.
That's a sweet spot for us. Those companies come to us to coach the entrepreneur to run the sales team. We build the system and the sales operating model with them, which is what we call our sales playbook, then they hand it off to somebody else. We've done that very frequently. We won't step in unless that owner-entrepreneur goes, “I'm in. We're going to be doing sales day one day a week. The funnel is coming in. We're going to be running it. We're going to be coaching the team, doing one-on-ones, and doing some training.” That's what I would suggest to the entrepreneurs that are tuning in.
It's super important to get that playbook in place. A lot of the entrepreneurs that find themselves leading a sales team are like, “I never signed up for this.” They want to bring in somebody that they see as a silver bullet to come in and formalize everything. That very seldom works. That person will come in, and they'll try to bring in whatever they were doing previously, which may or may not be a fit. You might get lucky. Many times, I've seen it fail. That’s a great point.
It's not fair on the person coming in. The cost of a failed new hire, particularly in an entrepreneurial environment, is so expensive. When you bring somebody new into a business, everybody spends so much time ramping them up and sharing information. You expose your client base to them, and then they don't work out. I've brought them out to the clients and all of these kinds of things.
That's my coaching for the entrepreneur. Try to build a playbook. You don't have to engage with companies like ours in consulting. Companies like ours have books that you can read for $25 or an online academy that you can go and learn from. Go to SellingWell.com. Any way you want to ramp up, go and do that. You have to walk in the shoes before you bring somebody else in to try and do it.
Staying Top-Of-Mind During Long Sales Approval Processes
That's great advice. Good stuff.
Thanks.
That’s a big topic.
Thank you so much, Sharon.
Let's move to number two here. For number two, we have Dan. Dan says, “I'm a big fan of the show. I love that you're doing these Office Hours episodes.” That's great. Dan says, “I have something for you that's a little bit more tactical, but I would love your feedback. Once we present a proposal, our clients usually have a pretty long internal process of approvals to shepherd it through to completion. How do I stay engaged with the prospect so that I'm not sitting there wondering what's going on without being a nuisance?”
Nice one, Dan. First of all, when they've got that long process, what you're always trying to do, through discovery, is build that relationship with the client where they get a sense that your primary goal is helping them. The whole intent of our sales process and discovery is that they get a feeling, and they understand truly that you're adding insight, value, and knowledge, and you're trying to help them.
Sales Career Advancement: The whole intent of our sales process and discovery is that they get a feeling, and they understand truly that you're adding insight, value, and knowledge, and you're trying to help them.
You only exit the discovery stage of a sales process when both you and the company believe there's a meaningful desired outcome for the company. There's an opportunity on the table. You both agree. You built a business case and a return on investment that makes this worthwhile for them, and then you do your best to prove that you can help them get there better than anybody else. The truth of it is the way you prove that you can get them better than anybody else is by knowing them better than anybody else. The whole process of discovery enables all of that.
When they then take it and go away, what you're trying to do through discovery is you're trying to work with them to understand, “What is going to happen once we put this together? How do you make a decision on this?” Try to get as much insight as you can. I can only do this after I've earned trust, built some credibility, and built relationships. Too many methodologies out there start to tell you, “I've got to qualify up front.”
Depending upon the size and scale of the offering you've got. You're going to be asking them at some point in time pretty detailed questions, like, “How do we get to a decision? Who's involved? What's important to everybody? Who's got what degree of influence?” Nobody is opening up and telling you all those things unless they completely see you as a consultant trying to help their business. Timing matters on this.
When you're doing all that in discovery, if this does go well, and you've earned the right for that kind of trust and credibility and earned the right to ask those questions, then you won't be seen as a nuisance. You're seen as a partner in the whole process. You might ask them and say, “How do we get from here to a decision?”
Somebody's going to come back and say, “I'm not quite sure. There's an executive steering committee meeting a week from now. First, I'm going to present it to my boss, and then they're going to go into the executive steering committee meeting.” You might help collaborate, think through that with the prospect, and go, “The last time you made a decision like this, what happened?”
I remember back in the day when we were working with you and the great team at RCT, Risk Control Technologies. Even having that kind of conversation, I remember you said that oftentimes, when you asked some of the buyers that question, they'd say, “We're going to go to my boss and then go to an executive steering committee, and they're going to make a decision.” You were smart enough to ask them, “When does IT get involved in this? How do they sign up?”
They were like, “Good point. Maybe we should include that in the process.” We've been burned so many times on somebody not including that in the process. It’s a great example.
That would be such a great example when you ask them that, and they go, “That's a pretty good question. I haven’t even thought about it.” It’s like, “I'm glad I brought it up.” First of all, they're saying, “Dave's not just waiting to figure out when he's going to get a signed contract. Dave is helping me do the right thing.” I remember you used to say, “How can I help you in that IT meeting?” I said, “We do this all the time. We know the 5 or 6 things you're going to ask and look for. Can I join you for that? Can I help in any way?” What a great way to slow down to speed up.
Specifically in a larger enterprise-type sale, the role of a salesperson is not to go in and be like, “Let's close these guys.” It's more like a project manager. I read a great book a little while ago. I don't know if you've read this one. It's called Selling With. It's by a guy named Nate Nasralla. The concept is that people think that salespeople are in there, closing deals.
He says over 90% of B2B selling happens during internal meetings. As a salesperson, how can you help the internal conversations move forward with you or without you in the room? It's a great read. It shifts the mindset, certainly of people who have that, “We've got to close this deal,” to, “We're here as facilitators. We're trying to help the prospect get this deal over the finish line. How can we do that?”
Over 90% of B2B selling happens during internal meetings. As a salesperson, how can you help the internal conversations move forward with you or without you in the room?
It's very similar to Brent Adamson. He was the original author, with Matt Dixon, of The Challenger Sale. There was The Challenger Customer and a couple of lead-ons. He wrote an article in HBR called Sensemaking in Sales that elevated to a book called The Framemaking Sale. We interviewed him on that. If you're tuning in to this episode, all you have to do is go back 4 or 5 episodes. We talked to him about it. It's the exact same thing. He said that the role of the salesperson is, first, you're trying to get an organization to say, “There's some pain we need to solve for.”
A lot of times, you're trying to say, “We want to give you confidence that we're the right company to help fix that pain.” He said that the real issue is you need to help the buying group get confidence that they're making the right decision. Not that they’re picking you, but they know they need confidence to make the right decision. It will inoculate against the biggest threat, which is the threat of doing nothing. They need to develop that confidence to make the right decision. When they're losing confidence, they do nothing. It’s an interesting topic.
The long and short of it is these things all keep coming back to this constant theme that says, “We're consultants. We have to calm down.” All those questions you asked about, “What's going on in the timing and the qualification?” Salespeople ask those questions because their boss asks those questions. The boss is trying to forecast deals and does nothing but say, “What's the qualification? Is it qualified?”
What we need to do is figure out how we work less, win more, and earn the right to be able to spend more time with the deals that matter because they are our ideal client profile. They're big enough for us. They matter. We know we can win because we add value. There's a lot of doing less and being better required in professional sales.
Good stuff. I love it. It's a good one, Dan.
Thanks, Dan.
Prioritizing New Business While Managing Existing Accounts
That was a good topic. Lots of good stuff. We got one more. We got Ravi here. Ravi says, “I'm a senior account executive. As part of my role, I'm tasked with bringing in new business as well as managing existing relationships to drive incremental revenue. I often find myself having difficulty prioritizing because my existing clients take up a lot of my time,” which I've seen before. He said, “The way our commission structure is set up is that I have more incentive to bring in new logo revenue. What are some things I can put in place to help me prioritize better?”
Let's spin it around. I got a lot of thoughts on this one. Why don't you start? What do you think?
Structurally, there is often the case where a sales rep is tasked with both of these things. As a company evolves and gets larger, they should scratch their heads to think about whether that's the right structure or whether they should have some kind of account management to take on existing clients. When you have somebody that's good at bringing in new business, they should be focused on that 100%.
Specifically on a tactical level for Ravi, think about time-blocking. It's like, “I'm setting aside Monday, Wednesday, half of Thursday,” or whatever it may be in terms of how much time you want to allocate. It's like, “I'm not doing anything in terms of existing customers. I'm only doing outbound.” Put your computer in Do Not Disturb. Do your research. Do your outreach. Put the blinders on and get that stuff done. That stuff is hard. You sit in a sales kickoff with 100 salespeople and go, “Who here loves prospecting?” There are not that many freaks that are putting up their hands up there, going, “I love being rejected all day long 90% of the time.” It's not that fun.
The real issue is you need to help the buying group get confidence that they're making the right decision.
That was my favorite answer.
It's so easy when you're doing both. It’s like, “A client emailed me. I better get back to them ASAP.” You’re tricking yourself into not doing the hard work. That’s the most tactical, simple way to address this. I would love to hear your thoughts.
I have a couple of thoughts. I agree on all fronts there. We're in this unique world where it is evolving. You do get someone who's not just an account manager and not doing outbound demand generation. It's a bit of a combination of both. Most organizations are coming and saying, “I need the revenue.” It's so hard to hit the revenue number.
There are always those spiffs for new logos. The first thing starts with basic territory management. Let's take a look at our client base. Let's say I've got 50 clients. How do I want to prioritize and spend my time with my existing clients, and then how do I prioritize and spend my time going after demand generation? It all starts with thinking through it first.
With my existing clients, how do I prioritize spending time with the biggest clients? I've got to do it. The second level is those clients that have the most upside potential. They might be my competitors' biggest clients where I get nickels and dimes. It's creating the short list and saying, “My job is to create sell cycles and grow business. How am I going to grow that business? Part of it is my largest clients. Presumably, there are other things I can be doing. Secondly, there are other clients that have been very little with us, but have a lot of upside potential. Let me get in and check that out.”
On the demand generation front, I have to prioritize the pursuit of that market. What happens with demand generation is anybody who's got a pulse, who responds to anything I do, salespeople are going to want this tendency to say, “I'm going to go after their new logo. I'll take the meeting. I'm going to work on it. I've got a friendly person. Our kids play soccer.” You're wasting time. We have to prioritize the account we want. It's much harder to get in front of those accounts and have that conversation, but if we do, the upside is much greater.
All new logos are not the same. We have to prioritize. Depending upon your business, your industry, how contracts are structured, renewal dates, and all those kinds of things, sometimes you are locked out of an account for a while. In other businesses, you're not. You can get in and start chipping away. Think about that. It always starts with this ideal client profile. Whether it's my existing clients or a new client, who's the ideal client profile for us? What's my value proposition to them?
One of the things that's a trigger for us is there are certain clients that are going to value what we do, and there are certain clients that won't. I'll use an example. On paper, you might be a $50 million SaaS business. You might have a large sales organization, and they need training and coaching. There are going to be behavioral aspects or more subtle aspects to that ideal client profile after I speak to the CEO.
Some CEOs will come to us and go, “I have the best product in the market by a country mile. My sales team is terrible. They should be doing way better. Come on in and train them. They either make it, or they don't, but I churned them. Who couldn't sell this product? Every time I go to an account, I win it.” Those kinds of CEOs have a view of the profession of sales. We don't agree with their view at all.
We have another type of CEO in the same company and the same sales organization who say, “I believe one of the competitive differentiations we have in our marketplace is we sell better than competitors. We're trying to help a client. We're not in love with our own product, but I do want to help elevate and invest in my team to make them better because we believe selling can be a competitive differentiation.” That's our client. That's the one we want to work with. It’s thinking through that ideal client profile for you and how you go through the pain of having that first meeting.
Team, another tactic for demand generation is not something people love. It's easier if you're in the Peloton. This is a very difficult thing to do. If you're isolated, working remotely, and trying to do it on your own, help yourself out. Book in time with your other four sales reps. It’s like, “None of us want to do this, but we need to. Every Wednesday, let's jump on a call at 8:00 in the morning with a beautiful cappuccino in front of us.”
“We're all going to share the twenty companies that we're going to reach out to. We’ll go around the room and go, ‘Does everybody have the name, validated number, and validated email?’ To the best of our ability, we validated them as ideal clients for us. We're all getting back on this call in two hours.” We're going to go around the room and go, “How many people did you reach out to? How many people did you have a live conversation with?”
“If you didn't get the live conversation, you had to leave a voicemail. Did you also complete your hat trick, which is to leave a voicemail, an email, and a LinkedIn note? Do the hat trick. Every time you reach out, do three things because you never know what somebody's checking.” It is going through that with a team and then getting back on at 11:00 or 10:00. Maybe we did it back with you.
We were also sitting in the same room together, so it was even more fun.
Somebody's going to have success.
It's not only that you get back on the call and you're sharing, “I got this great prospect.” You're also going, “You should have heard what this one guy said to me.” It’s commiserating a little bit and having a little bit of fun with it because it's a tough job, for sure.
It's a tough job, but you've got to keep doing it. There's slow prospecting, and there's fast prospecting. To me, the phone is still a fast-prospecting tool. It still does work. If you go to HubSpot, Salesforce, and all these places, always download their latest state of sales. It'll validate that you can connect with people and get a meeting with people. It takes professional persistence, for sure.
For slow prospecting, we love the idea of always building your network on something like LinkedIn. Don't connect and pitch, but do build your network of people and expand your base. If you're going into every conversation thinking about adding value, insight, and knowledge to the client or prospect, and you work very hard so you can be able to do that, from a mindset perspective, as long as you're giving, it's much easier doing demand generation.
One more thought for Ravi. The existing clients that are taking up a lot of his time, it's worth looking at that as well, as one more thing to say. What is this time being spent doing? Is it revenue-generating activities, or is he going to have lunch with them and build rapport? Not that you never want to do that, but you want to systematize that. Look at what you're spending your time on. Are you having lunch, or are you setting up a quarterly health check meeting to see where there's more opportunity in the account?
Maximizing Client Relationships With Strategic Health Checks
Thank you for bringing up the health check. Team, you can check out the health check component of the book. We talked about the health check meeting. There's also a video in the Selling Well Academy at www.SellingWell.com. Check that out. The idea of the health check is I'm setting up a regular quarterly touchpoint or twice-annual touchpoint with somebody where we're learning about them and their business, and then understanding their perception of how we're helping them achieve their most important desired outcomes. It does, at times, give us a chance to share what we're up to.
Sometimes, when you structure it this way, then when you do want to launch whatever, it can be pure relationship-building. You have that cadence to get in front of this important conversation with your existing clients so that you're understanding where they're going. That's going to identify for you, “Is there future opportunity within that account, or have we maxed out what we can do, and now it's about making sure service delivery is 10 out of 10? We're constantly building a moat around that particular account, so our competitors can't penetrate it.”
Your clients are much better when they prepare for those conversations and give you thoughtful feedback. They can't do that when you take them out for lunch and ask them off the cuff, “How are we doing?” There are a bunch of cognitive biases that are going to be entirely based on what happened to them. That was a great question, Ravi. It’s a challenge for all of us.
Another good episode. We had some good questions from readers. As you always say, keep them coming. There are no questions too big or too small. Whether you're an SDR all the way up to the sales leader or the CEO, a lot of this stuff comes down to the same principles. It's worth talking through this stuff.
It's one of the most difficult things in business. Most organizations out there, if you gave them truth serum, they wish they were growing faster. It's a hard thing to do. It's a tough business discipline for every business out there. It's probably not getting easier with uncertainty at the macroeconomic level and all of these things that come down. We appreciate your questions, everybody. Thanks for sending them in. When you see these links on LinkedIn, you can fire questions to either Dave Hanley or me, Mark Cox, through LinkedIn. We'll add them to the show. We'll see you next time. Dave, thanks as always for hosting these.
Thanks.
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