Your new salespeople aren’t learning what you think they are from your veteran people. It’s not the fault of the newbie or the veteran. Expecting someone to learn a non-transferable skillset by watching someone else exhibit that skillset is an onboarding problem, not a people problem. If you really want to help your new salespeople, give them a repeatable and documented OOH sales process.

Being an exceptional OOH sales leader requires more than achieving revenue goals. True leadership is about cultivating a culture of accountability, motivation, and growth while preparing your team to thrive in an ever-changing market. To excel, OOH leaders must hone four critical traits: coaching, motivating, accountability, and recruiting. Let’s explore how these skills can transform your leadership approach and drive success in 2025.

Retaining and growing your most valuable clients hinges on more than just delivering impressive results; it’s about delivering success on the customer’s terms. Central to this strategy is the cultivation of high-level client executive relationships, where value—defined from the client’s perspective—is at the heart of every interaction.To foster and sustain these critical relationships, regular client-executive meetings are not just recommended; they are essential.

There is no one-size-fits all sales coaching model. There are only approaches that have been shown to be successful in particular situations. As the coach, you must identify each individual salesperson’s personal “success code” – and use that code to unlock the salesperson’s potential for success. Here are five tips that have been proven to help OOH sales leaders unlock that code.

How you invest your time each day determines the degree to which you are successful in your personal and OOH business life. Create daily habits that make productive use of your time. Stick to your daily routines. Every productive minute pays dividends down the road in the form of heightened leadership skills and OOH expertise, good health and strong relationships. These daily habits have a cumulative effect which eventually shows up in the form of a greater degree of success than you ever realized you could have.

Most OOH leaders spend a large amount of time, effort, and energy looking for an applicant. The interview process is typically relatively short and usually consists of the leader being unprepared. Unprepared to ask pertinent, behavioral based information gathering questions that will allow us to have a greater insight into the individual that we are thinking of investing in by making them a member of our team. What’s the default for most OOH leaders when they are unprepared for the interview? Spend 90% of the interview time talking to the candidate about the company, the job, the kind of person we are looking for, the benefits we offer, how they would get paid, etc. And then the onboarding process is non-existent. Typically, people are welcomed into the company and then asked to spend time with a seasoned OOH veteran who is supposed to show them the ropes. Experience has shown that on its own, this is not an effective onboarding process. Not for salespeople, not for operations people, not for bill posters, not for real estate developers, not for anyone.

There is a concept I have talked about in a prior OOH blog post that is a very simple yet highly effective account management tool for keeping salespeople focused on what their priorities should be while working their entire book of business. It is called the KARE model, which is really just an acronym for the 4 basic “buckets” that we should group our clients in to better understand how to efficiently and effectively “handle our business” and serve our clientele. As OOH leaders we need our own “hack” to keep us focused on certain priorities to handle our business and serve our employees and customers.

As an effective leader you simply cannot allow your people’s problems to become yours. Once it becomes yours, they no longer have a problem. You can allow them to ask for advice and guidance on what their next step should be. Once that next step is determined they will own the responsibility of following through. These Monkeys rarely seem like such a big deal to help out with. Often, we think it is just easier to tell our people not to worry about it, you’ll handle it. They are distractions. These distractions, or monkeys, if not managed will stop you from achieving your own important goals or objectives.

‍Understand this about developing playbooks for each of the roles; you will not do this throughout the building in one day. It is a process. Begin with where in the organization do you believe it will have the biggest and most immediate impact. You will then methodically work through the organization until you have completed a playbook for every role. Secondly, you are never really done with this process. You must set a cadence of how long it will be (on a regular basis) before we review and update the playbook for each role and calendar block those dates.

Determining whether your sales culture is high-performing or broken requires a keen understanding of these key indicators. By assessing the clarity of purpose, communication dynamics, emphasis on learning and development, data-driven practices, recognition systems, and adaptability, you can fairly and objectively judge the health of your sales culture. None of this just happens—it's intentionally implemented through continuous and thoughtful efforts.

Go ahead, be honest, do you have any leadership blind spots that have slipped up on you over the years? Are you really leading your OOH team proactively or do you find yourself tending to “react” to whatever the day/week has in store for us? Blind spots can adversely affect you or any leader. Frankly, they’re easy to miss – and capable of causing immense damage without ever getting noticed.

One of the mistakes that we see often with leaders of OOH sales teams is that they spend an inordinate amount of their time working with the team members that are not performing at an acceptable level. Sometimes spending as much as 75% of their time on the weakest performing salespeople. Trying desperately to raise the bar on their performance, often they will by in large neglect interactions with the high performers on the team.‍It may sound counterintuitive to not focus all your efforts trying to improve the reps who have the most opportunity for improvement. However, think of it this way. If you have to lose a salesperson, who would you rather see go? The high performer or the one that never seems to come close to reaching the minimum level of production you expect. The most valuable investment you can make in your salespeople is your time, your attention, your guidance and your coaching. ‍While we are not suggesting that you shouldn’t work with and spend time with the under performing reps, we must avoid at all costs the perception that the only way to get your attention is to under perform.

Let me throw a couple of statistics at you that will blow your mind. According to a recent study conducted with hiring managers…1. 92% of hiring managers polled could not specifically describe what characteristics/attributes would be required for a new hire to be successful in the role they were hiring for.2. With the benefit of hindsight, those same hiring managers were asked what percentage of the new hires in the last 5 years would they confidently describe as “best fit” hires for their roles. Their answer? Less than 15%‍. How can you find the best candidates for your OOH sales position if you don’t really know what you are looking for?

Listening is a skill not everyone possesses naturally. While some excel in it, many find it challenging. As an OOH sales leader, effective coaching demands deep, empathic listening.

Salespeople fall into behavior-belief models categorizing them as high, variable, or low performers. Their position is shaped by behavioral choices and internal beliefs. Just as poor choices lead to low performance, positive choices and small, achievable goals propel salespeople towards higher performance.Embracing change becomes a pivotal factor in an OOH salesperson's success. The journey through denial, resistance, exploration, and commitment isn't just about adapting to new strategies; it's a transformative experience reshaping beliefs, behaviors, and, ultimately, performance. As salespeople and sales leaders navigate these stages of transition, they unlock the potential for remarkable growth and success, affirming that the ability to change is not just a skill but a crucial element of sustained excellence in the ever-evolving world of OOH sales.

The Success Triangle is a proven formula for OOH sales success – and a proven formula for every other kind of success. OOH sales leaders, and all leaders, can benefit from learning about this model and implementing it with their teams. So, what is it?‍ Those three corners on the Triangle can nurture your people. Those three corners can drive their ascent to their fullest and highest potential, not just in sales, but in life. Those three corners are a vital imperative for personal sustainable growth. Let’s look at each of them now.

In sales, where losses often outnumber wins, a cookbook becomes a valuable tool for maintaining self-esteem. By implementing a cookbook not only for your sales team but also for yourself as a sales leader, you'll likely witness a significant boost in your numbers. It's time to shift the focus from managing results to managing the behaviors that drive success.

As an OOH sales manager, your core responsibility is to empower your sales team to consistently excel and enhance their performance. Whether it's selling outdoor advertising or navigating complex negotiations for new locations, land leases, or easements, your influence is pivotal. Regular sales meetings, coaching sessions, and in-house training are integral components of your strategy to ensure your team is accountable, on track, and equipped with the necessary skills.

Have you ever taken a moment to decode what truly motivates each member of your OOH team no matter their role? Is it financial gain, the allure of status, or the thrill of achieving awards and goals? Motivation is a complex force, but it can be categorized into three overarching themes.

Ensuring your focus remains on these fundamental pillars can be the difference between good leadership and exceptional OOH leadership.

Enhancing the efficacy of your OOH sales team often requires more than just overseeing from the office. When you accompany them on sales calls, you're presented with an invaluable opportunity to see their skills and challenges in real-time. This first hand insight often reveals a more nuanced view than what's relayed during regular sales reviews. This isn’t to suggest that your team isn't honest; rather, personal interpretations can sometimes offer a colored view of events. By witnessing their interactions firsthand, you can pin point areas for growth and offer tailored support.

A bloated ego creates vulnerability for manipulation by others. If we subconsciously seek positive affirmation, it can render us predictable and susceptible to being led into decisions that harm ourselves, our team, and our organization.When we believe we’re the sole architects of our success, it can lead to being more rude,selfish behaviors, and a propensity to interrupt others. This attitude is particularly evident when faced with criticism or setbacks. An overgrown ego can obstruct our ability to learn from mistakes and hamper our appreciation of llessons derived from failure.Perhaps most damaging is that a large ego constantly searches for information that aligns with its beliefs. Essentially, an inflated ego can cause a strong confirmation bias. Consequently, we may lose perspective and find ourselves in a leadership bubble, where we only perceive and hear what we want, losing touch with the people we lead and ultimately our clients and land leaseholders.

‍We believe that early investment in active listening and development will prevent the need for continuous crisis intervention, aligning with Emerson's law: "To get more, give more." If you aspire to have a high-performing, self-reliant team, intentional listening and development are imperative. Otherwise, you risk perpetuating a cycle of constant intervention, forever echoing, "Up, up, and away. This is a job for Superman."

As a leader in the OOH industry, it is essential to evaluate the health of your sales organization by addressing these key questions. By focusing on pipeline health, developing remote selling skills, and safeguarding key customer relationships, you can navigate the uncertainties of the 2023 economy and maintain momentum for a successful year.

As a leader, are you effectively coaching your team? It's intriguing to come across leaders who claim, "I have highly experienced individuals who know how to perform well. I prefer to stay out of their way. If I have to get heavily involved, then I need different people." While this mindset is not uncommon, I've always found it somewhat puzzling. Americans have a strong inclination for sports and often idolize athletes in baseball, football, basketball, golf, and more. Isn't it odd that even the greatest athletes—Babe Ruth, Tom Brady, Michael Jordan, Tiger Woods—never went a day in their entire careers without someone coaching them to reach their peak and stay there? Yet, our experienced team members supposedly know what to do and don't require coaching; we should simply stay out of their way.

There are certain foundational aspects that must be in place if your OOH company is going to be as highly effective, efficient and as profitable as it can be. One of those things, in my opinion, is to have a culture of accountability. In our 40+ years of running media companies, training, coaching and providing executive coaching we have NEVER seen a company realize its full potential without a culture of accountability.

Many of our OOH clients have heard me tell the story of one of my great mentors I’ve had in my career. I still talk to him several times a year… and have for the last 40+ years! He had such a deep and profound effect on me that it would be impossible to overestimate his value in my life…professionally and personally.

There are certain foundational aspects that must be in place if your OOH company is going to be as highly effective, efficient and as profitable as it can be. One of those things, in my opinion, is to have a culture of accountability. In our 40+ years of running media companies, training, coaching and providing executive coaching we have NEVER seen a company realize its full potential without a culture of accountability.

A fallacy that many leaders buy into is that to be fair and equitable to the people who are part of my team, I need to treat each of them exactly the same. It’s understandable…most of us have heard some form of that most of our lives. I would beg to differ.