Delight customers and achieve your goals while saving up to 30% off the entire Insightly platform.
Best value– save up to 30%
CEO/Founder @ On Deck Leadership Consulting | Head of Growth @ Penny Finance | Head of Strategic Partnerships @ Unicrn
It’s midway through 2024, and you’re a new sales leader…congratulations! Now you’ve got to get to work.
The current and future state of the organization is on your mind. How can you make an impact right away, keep 2024 goals moving, and still begin to plan for 2025 quotas?
In this episode, Dave welcomes Meg Peterson of On Deck Leadership Consulting. They dive into the challenges of stepping into a new sales leadership role, highlighting the mistakes new sales leaders make and offering strategies to avoid them.
Tune in to learn how to successfully navigate your new position and make a lasting impact.
It’s the midpoint of 2024, which marks a pivotal moment for those in the tech industry. After a period of uncertainty, we’re witnessing a rebound with a small surge in hiring across all levels, from entry-level positions to executive roles. Sales teams are in a race to hit their annual targets, while leaders are already planning for the next fiscal year. This dual focus on immediate performance and future strategy creates a unique set of challenges and opportunities for sales leaders.
Meg, an experienced sales leader and leadership consultant, has some advice for sales leaders entering into new roles this quarter and beyond. One of the most common mistakes she sees new sales leaders make is rushing to implement immediate changes to prove their value. It’s understandable—joining a new organization, especially one that’s struggling, brings immense pressure to demonstrate impact quickly. However, this approach can backfire.
New sales leaders often feel compelled to apply strategies from their previous roles without fully understanding the current company’s unique circumstances. This knee-jerk reaction might stem from a desire to show quick results, but it can lead to unforeseen consequences. Meg advises taking the time to evaluate the existing processes, identify what’s working, and understand the reasons behind any inefficiencies.
For instance, a company might be struggling because it doesn’t fully understand its Ideal Customer Profile (ICP) or the reasons customers choose their products. Implementing changes without this crucial insight can disrupt effective practices and damage team morale. As Meg points out, the last thing you want to do is remove a team’s lifeline without grasping the impact on their daily operations and overall success.
To avoid this pitfall, new sales leaders should prioritize learning and assessment in their initial phase. Engage with the team, understand the current state, and identify both strengths and weaknesses. This thorough understanding will enable you to make informed decisions that drive sustainable success.
Remember, effective leadership isn’t about making rapid changes to showcase value—it’s about understanding, planning, and executing strategies that foster long-term growth.
Starting a new role as a sales leader is both exciting and challenging. It’s a time to make your mark, but without a solid plan, it’s easy to get off track. The second misstep many new sales leaders make is failing to build a 30-60-90 day plan. This roadmap is essential for aligning your efforts with company goals and ensuring a smooth transition.
Meg stresses that managing the expectations of the CEO or direct supervisor is key when stepping into a new role. Instead of rushing to implement changes from day one, it’s important to first understand the current landscape—identifying what’s working well and what needs improvement. This initial assessment guides the prioritization of tasks and necessary adjustments.
A well-crafted 30-60-90 day plan is more than just an interview formality; it’s a practical tool that serves both the leader and their team. This plan should outline clear goals and stretch targets, encompassing elements like change management, immersion into company culture, and customer engagement. The first 30 days should focus on immersion and understanding the status quo.
Having this plan ensures that new leaders have a structured approach they can confidently execute. It should be actionable and designed to add value, not so flexible that it loses effectiveness.
Meg’s advice is straightforward: create a detailed plan, adhere to it, and use it as a foundation for making informed, strategic decisions that drive success.
Clear communication and information sharing are the lifeblood of successful sales leadership, especially in the early days. This leads us to the third mistake of new sales leaders—keeping their 30-60-90 day plans a secret.
Instead of keeping your plan under wraps, Meg suggests sharing it widely. Ensure your intentions and the steps you plan to take are clear to everyone. This includes aligning with the C-suite and your executive team to gather their input and confirm that your plan supports the overall business objectives.
Printing out or emailing your plan to key stakeholders can foster collaboration and buy-in. Playing the “new card” allows you to ask foundational questions and gather insights from those who know the company better. No new leader is an expert on day one, so use this period to learn and refine your plan with feedback from others.
Meg also suggests regularly referring back to your plan in discussions with executives and team members. When new ideas or tasks arise, use the plan as a reference point to determine if adjustments are needed.
As Meg advises, being transparent about your 90-day plan not only provides clarity and alignment but also demonstrates your commitment and strategic approach, fostering trust and collaboration within the team.
Imagine having a treasure trove of information that could shape your product development, refine your marketing strategies, and propel your business forward—yet ignoring it. Listening to customers isn’t just important; it’s absolutely essential. Without their insights, sales leaders miss out on the very feedback that could drive growth and enhance their sales approach.
This leads us to the 4th mistake new sales leaders make—neglecting to connect with customers.
It’s easy to get caught up in the operational aspects of the business, but missing the chance to engage with customers can be detrimental. Whether through live Voice of Customer (VOC) interview calls, in-person meetings, or utilizing technology like Gong or Chorus, listening to customers should be a priority for new sales leaders.
Meg highly encourages new leaders to listen to recorded sales calls, as this practice helps understand the skill sets of the team and the problems the solution is trying to solve. And don’t just tune in to the closed/won calls; also review conversations where the deal was lost. Understanding why customers choose to buy—or not buy—offers deep insights that are often overlooked.
Additionally, reviewing customer surveys, net retention scores, and feedback from marketing and UX/UI surveys is essential. These insights reveal why people are attracted to the product, why they convert from leads to customers, and why they remain loyal.
By thoroughly understanding customer feedback at every stage, sales leaders can make more informed decisions and build stronger, more effective strategies.
Creating an environment where your team feels heard is crucial for any new sales leader. Effective listening isn’t just about gathering information; it’s about building trust, fostering team cohesion, and driving collective success. Neglecting this can lead to a disconnect between leadership and the frontline employees who are the backbone of your strategy.
Meg highlights that, while communicating with customers and stakeholders is essential, actively listening to your team is just as important. Failing to do so is mistake #5.
In the first 90 days, listening should take precedence over action. You need to listen up the ladder, down, and laterally.
Upwards: New leaders should absorb how the executive team communicates and resolves issues, asking insightful questions to gain a deep understanding. This learning phase helps in aligning with the company’s culture and operational dynamics.
Downward and wide: Engage with team members at all levels, ensuring they know that changes will be made with them, not to them. Creating an environment where team members feel comfortable challenging and contributing ideas can significantly enhance team morale and effectiveness. Listening to their concerns, ideas, and feedback helps build a collaborative plan moving forward.
Meg suggests sitting down with as many people in the organization as possible, especially within the revenue department and across other functions like finance, product, and customer service. Building these relationships early sets the stage for strong, future collaboration and trust.
So you’re new sales leader, now what? We’ll hear from a top consultant on the things not to do in this episode of Closing Time. Thanks for tuning in to Closing Time. The show for Go to Market Leaders. I’m Dave Osborne, chief sales officer at Insightly CRM. And I’m joined today by Meg Peterson, fellow Austin, Texas native CEO and founder of On Deck. Leadership Consulting. Thanks for joining me. Happy to be here. Now, Meg, this seems like a pretty opportune time for us to be having this conversation as we’re just about at the exact midpoint of 2024. Yeah, absolutely. We are seeing a great transition back to tech is rebuilding. We’re starting to see more hiring at all levels from BDRs up to executives. We are in that final push of, like if you’re going to make your 2024, if you’re working off of the calendar fiscal year, it’s make it or break it time. People are laser focused on doing what it takes to get the job done, to hit plan. But also leaders are moving into planning for 2025. It’s time to look at your comp plans, your quotas, your team make up, your skill sets, making sure that you’re set up for success. And that leads to having a lot on your plate as a sales leader. As much as we want to say like, oh, you know, I’m either really a player coach or I’m not really a player coach. We are all responsible for revenue and we’re there to engage with our customers and drive our sales teams to success, which means we not only we building pipeline, we’re on calls with customers, we’re on calls internally to get the sales to the finish line, which means you’ve got to have a plan. 100%. So a lot of folks may be looking to transition jobs, start new jobs, both individual contributors and leaders. But maybe let’s just focus on leaders just for a second and it will jump right into like five things or common mistakes that new sales leaders make when they join a new business. Right. All the mistakes I made. Right. I think we’ve all made them right. And that’s why we’re talking about it. So hopefully you can learn from our gray hair a little bit. But I think mistake number one, right, is coming in and trying to make an immediate impact and make changes all over the place just to show that you’re providing initial value. So that’s item one. Yeah. I mean, reality is, is as any leader, especially sales leaders, we expensive and we know that about ourselves and we have a lot to prove as sales leaders especially for joining an organization that is struggling. And so the knee jerk reaction coming in as a sales leader is to say, well, this worked over here at X, Y and Z organization that I was with, so we’re just going to do it here and not taking the time to actually understand what is status quo today, what is working in the organization and identifying what’s not working, but the why behind it. It could be anywhere from they don’t actually understand their ICP. I just read an article from a great sales leader around not understanding why customers are buying from you. Like what is that repeatable motion? It could be all these different things. You gotta take the time in the beginning to understand current state, so you make informed decisions of change, but also what that change will impact. The last thing you want to do is rip out someone’s life line and have no understanding of what that means to their day to day life or their ability to be successful. Totally. And I think along with that, it’s potentially managing expectations of the CEO or whoever you may be reporting to in that regard, too. That I’m not coming in and changing day one. I think first I want understand like what’s going well that we can continue to invest in and what’s broken. And then from there kind of deciding like prioritization of what tasks, what things we can change. And going from there. And I think on that from a planning perspective, maybe sounds cliche, right? Like when you talk about maybe going through the interview process, you know, a lot of folks will kind of put together a 30, 60, 90 plan to present to show that you’re buttoned up. But in practicality, failing to build a 30, 60, 90 plan seems to be a common pitfall as well. Yeah, it’s just as much for you as it is for other people. But you should have a plan that you’re comfortable executing on. It should have stretch targets. Change Management will be in there, your immersion plan will be in there, engaging with customers will be in there. Like all these key things that are so important in your first 90 days. But just like we were talking about, get immersed, understand status quo, that’s your, one through 30, it should be around that, but have a plan, build it and stick to it. Don’t make it so fluid that it’s not actionable or that it doesn’t impact and instill value. Well,. I think along those lines as well is, and this kind of leads into number three. Right. Make sure that plan isn’t a secret. Right. Like make sure that people are aware of your intentions and how things are going to piece together. Right. I mean, I would imagine that’s got to be a part of it or something I’ve seen or heard of other sales leaders make that mistake as well. Yeah. I mean, I absolute like print it out. Send it out, align with your C-suite and your executive team because your new like and you should play that new card, play that new card for the first 90, 2 years. I don’t know however long you want to play. As long as you can.. Ask the dumb new person questions. Yeah as long as you can. But you’re coming into a business that you do not know. There is not a, there’s nothing in the world out there that’s going to make it to where you walk in and you’re the expert at that company on day one. Talk about your plan with people, align with them. Ask them if that makes sense with your executive team, with your executive team, Talk to them about, hey, like, does this match your plan? Does this derail you? What would these changes mean to you? Engage and align in that way and then overcommunicate it? Always bring back your conversations to that plan. I know for me, I’ve lived in the startup world for a long time. It wasn’t uncommon for me to get with my CEO and the CEO so excited that you’re there. And it’s just like every time you meet with them, it’s just a laundry list of things that they want to do. Talk about it back to that plan. Hey, I love all these ideas. I think this is a great direction for us to go. Are these ideas more impactful than the current plan we have in place? Should we reprioritize? Are these things that are achievable now, or is this looking six months to a year in advance? Like have those tough conversations, over communicate that plan in your progress to it. So when someone asks,. I don’t know about you, but as a VP, I know people have been like, well, I mean, you know, she’s not closing deals, so what is she doing? You can say, I’m doing this,. I’m doing this plan. This is what I’m focusing on in the first 90 days. And it just gives you that leverage and that collaboration that’s so important as you enter in as as the new leader on the team. Supercritical communication, supercritical. I mean, not even just the 30, 60, 90, but I would argue, you know, managing up, managing down, managing, you know, laterally as well, that those comms are so critical. You know, another thing that I think a common mistake that some people, because they get so caught up in maybe the operational aspects of the business is connecting with customers. Right. Missing the chance to talk to them. You know whether be, you know, live on calls, in person, or using like a Gong, a Chorus, you know, technology. But I’d love to hear your kind of your thoughts on, you know, where that fits into the plan. Yeah. I mean, Voice of the Customer is truly the most impactful thing that you can have in any growing or existing successful organization. You know, voice the customer comes in in a lot of different ways. I highly encourage leaders entering in a new opportunity to take the time to listen to past sales calls. It’ll help you understand people’s skill sets too. So it’s kind of helps check two boxes, but listen to past calls, understand the problems that this solution is is attempting to solve for your for people in your pipeline. Listen to calls of people who didn’t buy, listen to calls of people who did buy. A lot of people miss that stuff. I don’t know why, Voice of the Customer isn’t just why you lose, it’s why you win, too. Like really getting a deep, core understanding of why people have purchased that software, That product to date before you arrived is really valuable. And then view the surveys, get with your CS leader, look at if they have, you know, any type of net retention score or survey or any type of surveys from marketing that have gone out, UX UI surveys, all those different things like go read about why people are coming in as strangers, converting to leads then customers and staying on to influence and be customer advocates like understand why at each stage. And speaking of communication. Right? I think we’ve talked a lot about, you know, communicating internally, connecting with customers. But I think, you know, there’s also an important element to this, which is listening, right? So missing the chance or you’ve got to try to foster an environment of feedback. Right. And listening as an executives, sometimes maybe you’re doing a lot of things, but making sure you have an ear to the ground and a pulse of what’s happening seems to be a pretty critical part of the puzzle as well. I think especially in the first 90 days, listening is more important than action and talking in a lot of scenarios. So we talked about managing up, managing down. So let’s talk upwards first. You are the new leader in a team. You were brought in to solve a problem or to keep momentum going. But you should learn from your executive team and your C-suite about how they engage each other, listen to how they talk, how they solve problems, how they resolve conflict. Like all these different things. So listen, really just be a sponge, ask good questions. Don’t just say yes or no. Say, that was really interesting that you went so deep into this area. Has that been an issue in the past? And get to know that core information, Then we talk downwards, Downwards and wide. Downwards and wide. So as you’re listening, like you want your team to know that you’re not coming in and changing their whole life. You’re not going to come in and do things to them, you’re going to do things with them, you’re going to guide them to this new level of success, which means you got to listen. You got to create an environment where they feel comfortable to challenge you and to make you better and to help you learn. And to do that, you have to listen to, you know, you’re going to get some people who you listening to them is you listen to them complain, you’re going to get some people who come to you and they are so junior that they want to be a sponge, too. And just take the time to learn where they are at today. Their ideas, where they see gaps and then use that to build your plan for 91 days on. It’ll help you build that team culture of my leader is here to support me versus I’m here to support my leader. Yeah I mean supercritical to get that going from day one. Right. And something one of my mentors taught me or showed me when they joined a company and I’ve done subsequently when I’ve joined other companies is where possible, obviously depends on the size of the company. But I try to sit down with most people that are in the business. Definitely everyone in the revenue org, but also cross-functionally like leaders across departments, right? Sales is a team sport. It takes everybody finance, product, CS to make this thing work. So why not just start those relationships now, right? Build those like understand what’s going well, what’s not going well? Build that connective tissue. I mean, you’ll have a major kind of trust factor upfront, but I think it sets the stage for how that relationship could be going, you know, in the future as well. Yeah. I think there’s also just a slight misconception about VPs of sales right now out there in the marketplace, which is what I think that they’re saying now the average tenure a VP of sales has at an organization’s 18 months. That perception alone changes how people will go, even if that’s not true, I don’t know a single VP of sales who walks in the door somewhere and says,. I’m only going to be here 18 months. I mean, no one’s no one’s going in with that. So, you know, the more we can fight that perception, the more that we can show that the VP of sales is meant to be the heartbeat of this customer led growth motion, the stronger your relationships will be with people that you know, your executive line, the people that are leading other cohorts within your organization, but also your team will follow you with loyalty because they know that you are there for the long haul, regardless of what actual date you end up leaving the organization. I couldn’t agree more. I love that. Well, thanks, Meg. That’s all the time we have for this episode, but really appreciate you joining us and sharing those insights. I would love to being here. Thank you so much. Awesome. And thanks to all of you for tuning in. Remember to like this video. Subscribe to the channel and tick the bell for notifications so you don’t miss an episode. We’ll see you next time on Closing Time.
