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Stop Selling, Start Asking

Posted on | Author Gary Pica

I was talking to one of our TruMethods Peer group members this week. I spoke to this MSP leader about a sale they were working on. The prospect was deciding between them and one other MSP provider.

This MSP was about $500 to $1,000 more per month than the competitive MSP. That’s a meaningful price difference that would make any prospect pause and really consider their options.

They had made some headway reframing the decision maker, but the office manager had shown some reluctance. They wanted details about what tools our member used and some other technical details. You know how this goes — when prospects start asking for technical specs, it usually means they’re looking for reasons to justify a decision they’ve already made.

So, our member decided to set up the next call to sit one-on-one with the office manager before meeting with the decision maker again. Now, there were some good things here. They had a ‘next step’ that they controlled. That’s awesome. Having control over the next meeting is always better than waiting for the prospect to get back to you.

But I asked a few more questions like: Was not knowing their tool set really the issue? What if the tools weren’t actually the roadblock here?

In general, how had he felt about what you explained in terms of your approach and what he had heard from the other vendor? Assume that he had seen your tools and technology, and thought they were all fine. Then, who would he have chosen and why? This is the question that cuts through all the noise and gets to what really matters.

Our member said he didn’t know because the office administrator never said. And there’s the problem right there – they were having a conversation without ACTUALLY having a conversation.

This is the information you need to help this prospect decide and to know where you are in the sales process. And all you have to do is ask. The prospect wants to make the right decision, but they need your help to get there.

So many times, it’s that simple. Just ask for the information you need to help the client decide. Most prospects will tell you exactly what they need if you create the space for them to do it.

Too often, business leaders and salespeople are so busy selling that they don’t stop to just ask. We get caught up in our pitch and forget that selling is a conversation, not a presentation. There are two common mistakes: the first I call “shotgunning,” or just telling the prospect countless things that are great about you and your offering, hoping that some will stick, or assuming that you know what the prospect is thinking or feeling. The second mistake is even worse — we make up stories about what the prospect is thinking instead of just finding out.

When you know where you really stand, you can focus your energy on the deals that actually have a chance to close. Try selling less and asking more. Your stress level will go down and your MRR will go up.

You’re Already There, So Why Not Be Awesome?

Posted on | Author Gary Pica

Every business owner wants the same thing: a better business. They want to grow faster and be more profitable. And every employee wants a better career. They want to make more money, be recognized, and maybe earn a promotion.

Here’s the problem: I’ve seen thousands of business owners who want the same things, but they’ve gotten very different results. They all get up early. They all go to the office. They all work hard. They all think they “deserve” success because of the effort they put in. But effort alone doesn’t entitle you to results.

Our parents told us that if we worked hard, good things would happen. My father worked in a factory for 35 years. For him, showing up and working hard did mean job security. But if you’re a business owner or knowledge worker, that old formula doesn’t work. Just showing up isn’t enough anymore.

Over the past 30 years, I’ve managed hundreds of employees, and today I work in a 5,000-person company. I’ve seen it over and over again: people who believe that showing up, working hard, or simply doing their best should automatically create great outcomes. It doesn’t. Results are what determine success in a job or in a business.

For employees, that means you need clarity. What does success in your role actually look like? If you don’t know, you need to get aligned with your manager immediately. For business owners, it’s the same—define what success looks like for your business and measure yourself against that definition.

Too many people use effort and comparisons as their scoreboard:

  • “I work harder than him.”
  • “I’ve been here longer than her.”
  • “I come in earlier than they do.”

None of that matters. Success comes from outcomes, not effort.

So here’s the shift:

  • Take full responsibility for results.
  • Look for creative ways to improve your role instead of waiting for direction.
  • Make the people around you better.
  • Don’t just point out problems—bring solutions.

In my experience, that’s the difference between people who grow and people who stay stuck.

I have a saying: everyone makes exactly what they’re worth, whether they like it or not.

You’re already up. You’ve already showered, eaten breakfast, and made it to your desk. You’re already there, so why not be awesome?

The Discipline Behind the Champion: Mastering the Mindset for Success

Posted on | Author Gary Pica

Everyone dreams of being a champion—but the truth is, only those who commit to the journey truly become one.

Simply put, you can only be a champion with self-discipline. There’s no magical shortcut or secret formula to becoming the best at what you do. Success is cultivated through the right mindset, attitude, hard work, and discipline.

When someone tells me they want to be a sales champion, I ask, “Do you get to work on time?” It’s not a trick question, but a reflection of readiness. Punctuality may seem small, but it’s a powerful signal of commitment. If you’re not showing up consistently, how can you expect to lead, inspire, or win?

Throughout your career, you’ll face challenges that require more than just skill—they’ll demand resilience, ownership, and a willingness to grow. Being on time isn’t just about the clock. It’s about honoring your word, your team, and your goals.

If self-discipline feels like a struggle, you’re not alone, and you’re not stuck. One of the ways I stay disciplined is by creating self-instruction cards and reading them daily. I’ve done this for decades and continue to do it to this very day. Self-instruction cards serve as a personal accountability tool.

Here’s how to create them:

  • Start with a collection of 3×5 index cards.
  • On each card, write from a first-person perspective, as if you’ve already mastered a specific trait.
  • Provide detailed descriptions and integrate emotions to make the narrative more vivid.
  • As you grow and change, adapt your deck by adding new cards or removing those that no longer apply.

Consider a card that emphasizes punctuality: “I am always 10 minutes early to work. I am 100 percent ready to start my day on time because my team and customers depend on me. Most importantly, I depend on myself.”

Champions are made through their daily habits, steadfast routines, and an unyielding commitment to discipline, establishing the groundwork for triumph well before any accolades are received.

Why Everyone Needs a Financial Plan (No Matter Your Income)

Posted on | Author Gary Pica

We all live in a world where money has a significant impact on our lives, both in the short term and the long term. It holds more power over us and how we feel about ourselves than we’d like to admit. And here’s the interesting thing: just having more money doesn’t solve the problem.

I’ve seen people with six-figure and even seven figure salaries stress about money just as much as those making minimum wage. That’s what makes money so tricky.

It’s not just what you have — it’s more about what your expectations are. Your lifestyle tends to expand to match your income, regardless of how much you earn. This is why I believe that everyone needs a financial plan, no matter their net worth or income level.

A well-thought-out plan does two things for you. First, it reframes the present and helps you make better short-term decisions. When you know where you’re headed, it’s easier to say no to impulse purchases and yes to investments in your future. Second, it can also relieve some anxiety around money.

Think of it like having a clear roadmap — you might not love every step along the way, but you’re building toward something meaningful.

However, you might not like some of the outcomes. Maybe you need to spend less or do without certain luxuries. But here’s what I’ve learned: temporary sacrifices lead to permanent choices. The plan also allows you to spend extra money without guilt. Once to contribute to your plan, it’s ok to spend the rest on luxuries, experiences, and charities.

Since I was thirty years old, my plan only had two main goals: send my kids to college and have choices later in my career. That’s it. Simple, clear, measurable.

This informed my income goals, spending limits, and net worth targets. It also forced me to value my time differently. Every decision was filtered through these two priorities.

Over time, I’ve accumulated a few trimmings and trappings, but only after my two primary goals were met. Your goals may be different, but I think we all want choices as we get older. Maybe it’s scaling your business, taking calculated risks, or having the financial cushion to pivot when opportunities arise.

If you don’t already have a well-thought-out long-term financial plan, I suggest you work on it. Start simple. Write down two or three things that really matter to you. There are tons of resources in the form of books, podcasts, online resources, and financial planners.

The best time to plant a tree was twenty years ago. The second-best time is today.

People who plan tend to achieve significantly better financial outcomes over time. It’s not about being perfect—it’s about being intentional.

Success Changes How We Remember the Journey

Posted on | Author Gary Pica

Recently, I spoke with Tim Fitzpatrick. If you don’t know Tim, he was working at the MSP that I bought into in 1996.

I met him on my first day, and that kicked off a thirty-year journey across three businesses: Dynamic Digital Services, TruMethods, and now Kaseya. It’s amazing how one conversation can transport you back through decades of memories.

We spent about 45 minutes reminiscing about the past. We laughed about so many funny situations along the way. We both commented on how lucky we feel for our careers.

I look back with such fondness and gratitude.

After we spoke, I picked up one of my journals from those early MSP days. I was struck by how many of the entries I shared were about how difficult things were in the moment.

Financial stress, people problems, and a few near-death experiences for the business.

I found entries where, early on, I questioned myself and wondered if I was good enough to see it through. The doubt was real, and it felt overwhelming at times.

I spent the rest of the evening thinking about the contrast between my conversation with Tim and my journal entries.

What I concluded was that success determines how we feel about the past.

The setbacks, the doubt, the frustrations fade, and all that’s left is a feeling of accomplishment.

I know people who went through the same struggles as I did back then and didn’t achieve the same level of success. They feel very differently about their careers. Their stories remind me how fragile confidence can be without wins to back it up.

Here’s my point: You may be going through a tough time in your business. Maybe you’ve been in business for several years or many years and never achieved your potential.

You might be questioning yourself right now.

I get it. I’ve been there. It just takes a little success to build on, then a little more to change your expectations, and six to twelve months later, you can be on a new path.

Maybe you need to increase your value and pricing to your current customers or add some new logo customers at the right price.

You might have trouble taking action in these areas.

Just approaching three customers to explain your new value and having one of them say yes is a win. That single yes changes everything — your mindset, your confidence, your momentum.

You can develop some COIs and get one good lead. Even if you don’t close it, you’ve changed your expectations.

Nothing succeeds like success.

So, here’s what I want to tell you. Whatever you may have experienced in business, if you can reach your goals, you will look back over all of it fondly. And here’s the best part: you get to keep that feeling for the rest of your life.

That conversation with Tim reminded me that the struggles we’re going through today will become the stories we laugh about tomorrow — if we just keep pushing forward.

The Summer Mindset That Separates Winners from Excuse-Makers

Posted on | Author Gary Pica

We are currently in the summer season, and for many businesses, this can be a make-or-break time of year.

This is a time when people take vacations and enjoy some time with family and friends. The pace feels different and more relaxed. But your customers and prospects are still out there, still making decisions.

I know my schedule changes during the summer with a priority on leisure activities, and I think it’s awesome. Something is energizing about longer days and that summer feeling. I’m not saying you should skip vacations or avoid time with family — those things matter tremendously.

At the same time, we need to maintain a focused approach to our goals and quarterly initiatives. The key is finding that balance between enjoying summer and staying committed to your business objectives.

We need to meet our sales goal, achieve our professional services billing goals, and ensure that we don’t use the summer schedule or vacation as an excuse for not doing so.

The numbers don’t care what season it is.

We need to plan to achieve our milestones every quarter. Reaching goals and achieving your quarterly rocks can be part of having a great summer. It’s all a mindset. When you hit your targets, that vacation feels even better. There’s no guilt, no stress about what you should be doing instead of relaxing.

I learned a lot about this early in my sales career. As a young salesperson, I was part of a few very large sales organizations. I was eager to learn and watched everything closely. What I discovered was fascinating — there were really two types of salespeople during the summer months.

I noticed that most salespeople often used summer, holidays, and vacations as excuses for not meeting their monthly or quarterly sales goals. It was always something — kids were out of school, people were traveling, decision-makers were unavailable. The excuses were endless and creative. But here’s what was interesting: The prospects and customers were still there, still buying — just from someone else.

I watched others achieve consistent results every month. I saw how they always had a plan that factored in external issues or events. They understood that business doesn’t stop just because the weather gets nice. These top performers knew that while others were making excuses, they were making money. They treated summer as an opportunity, not an obstacle. This is a great lesson to learn, and I brought it mentally into my career as a business leader.

Take time to think about this and make sure everyone on your team does as well. Set expectations early and get everyone aligned on what success looks like. And make the decision that you and your team will get results four quarters every year. That’s what separates good teams from great ones.

The best teams don’t have seasons — they have standards.

Look, summer will come and go whether you hit your goals or not. But which version of yourself do you want to be come September?

The one who enjoyed summer and crushed their numbers, or the one who has to scramble to catch up?

The choice is yours.

Why Old Beliefs Limit Your Growth Potential

Posted on | Author Gary Pica

Flat Earthers believe the Earth is flat, yet many of these same people accept the Big Bang theory, which proposes that the universe was once the size of a marble. They reject something with overwhelming, definitive proof while embracing something theoretical. We have photographs of Earth, but none of the universe before it came into existence.

We see this same phenomenon play out every day. In our current political climate, the effort to believe false claims often exceeds the effort to find truth. This pattern extends into business, where our beliefs can similarly cloud our judgment. Some of you approach key areas of business and achievable results as if the Earth were flat, rejecting clear facts while readily believing that a new service manager or salesperson will theoretically solve all your problems.

In all these cases, we’re choosing ideology over facts. We cling to the history that brought us here, protecting it even when our results clearly show we haven’t reached our goals or met our needs. This attachment to comfortable beliefs over challenging truths holds us back from genuine progress and innovation.

Speaking of challenging beliefs, I was recently reminded of this during a Peer group meeting. Our group is filled with people I trust, respect, and care deeply about. One member presented a burning issue, and the responses were passionate. Everyone had strong feelings, with several views directly opposing each other. I found this fascinating. Despite having my own strong opinion, it made me pause and question whether I needed to think differently. Ultimately, the member who raised the question shifted their perspective based on our discussion.

This experience reminded me of something I’ve observed throughout my career: The most successful business leaders aren’t necessarily the ones with the most knowledge or experience, but rather those who remain open to changing their minds when presented with new information. They understand that protecting their ego is less important than growing their business and developing their team.

Think about the last time you encountered a business challenge. Did you immediately jump to solutions that felt comfortable and familiar, or did you take time to question your assumptions? Were you willing to consider that your usual approach might be part of the problem rather than the solution?

Challenging closely held views is central to fulfilling our potential. While this can be difficult, I’ve observed that it becomes easier with practice over time. Unfortunately, some people never develop this skill, limiting their potential and damaging relationships. We should all view this as an essential skill to develop.

The truth is, in business, as in life, being right isn’t nearly as important as being willing to learn. Every time we defend our position without truly considering alternative viewpoints, we miss an opportunity for growth. Every time we dismiss new ideas because they don’t fit our existing beliefs, we potentially leave money on the table and limit our company’s potential.

I’ve seen companies transform when their leaders finally let go of long-held beliefs about what’s possible or impossible in their market. I’ve watched struggling businesses turn around when owners stopped believing their industry was “different” or that certain changes “wouldn’t work here.” These transformations always begin with the willingness to challenge our thinking.

Remember — growth begins when certainty ends.

Navigating the Greatest Transition in Our Business Model

Posted on | Author Gary Pica

Our business model is approaching its greatest transition. AI and automation will impact every aspect of our business and our customers’ business. This isn’t just another tech trend—it’s a fundamental shift in how business gets done. For those of us who have been in the business for thirty years, like me, the only technological advance that can be compared to this is the emergence of the Internet.

This transition is moving even faster because it’s becoming popular now to the public, but it’s been under development for many years.

So, how do we win on this transition?

We can look at past transitions in our space and learn some lessons, like the changing security landscape. Looking back at those successful transitions, the MSPs that won had some shared characteristics.

They were already operationally mature. They had a sales and marketing function, and they had a strong vCIO process. These weren’t just nice-to-haves. They were the foundation that allowed successful MSPs to pivot quickly and capitalize on new opportunities. So, these are prerequisites for your ability to operationalize changes in an MSP and monetize the changes. But operational maturity alone isn’t enough.

The second critical factor is speed. The companies that get there first usually win. They establish a lead and never relinquish it. So, how do you get there first?

Start with education. Read. Collaborate with others who are further ahead. Find vendors in the space that are leading the way. Attend conferences, join forums, and get hands-on experience with the tools. Don’t try to figure this out in isolation—the learning curve is too steep.

Then, make a plan to use AI and automation in your business—not just service delivery, but all areas of the business. Look at your sales processes, marketing automation, project management, and even HR functions. When you’re ready to implement, focus on support desk and ticket reduction to impact efficiency. This is where you’ll see the most immediate ROI.

Put measurable metrics in place to track your progress. You need to know what’s working and what isn’t, because this technology is evolving rapidly.

As you build internal capabilities, begin to talk to your customers about where they are in terms of their automation journey and develop questions that uncover opportunities with them. Your customers are facing the same pressures you are, and they’re looking for partners who can guide them through this transition rather than vendors who are still figuring it out themselves.

Winning starts with getting there first and understanding how we lead the way with automating our customers before someone else gets there.

Remember that this transition is happening with or without us, so we are either gaining a competitive advantage or we are losing one. There’s no standing still in this environment. Doing nothing has a lot of risk.

An Owner’s Responsibility

Posted on | Author Gary Pica

I believe that owning a business comes with significant responsibility — not just the responsibility of managing the tasks and details required to run the business, and not just the responsibility to your customers who rely on your services.

Your primary responsibility lies with the people who work for you. At a basic level, this means providing a safe, non-toxic work environment where employees feel comfortable working every day. It also involves giving them a well-defined role, so they understand what success looks like. Beyond these basics, there are two other critical areas of responsibility.

The first is creating opportunity and growth. The only way to achieve this is by growing your business — specifically, adding new customers at the right price. Consistent growth is essential for long-term success, as it enables you to provide new opportunities for your team. Without growth, you cannot offer your employees the chance to advance.

The second is helping loyal, long-term team members achieve financial stability. This requires running a highly profitable business and educating your team. For example, at TruMethods, we offered a 401(k) program with two different profit-sharing plans for our employees. Each year, we invited our 401(k) provider to educate the team on planning for their financial futures. We could do this because we maintained a very profitable business.

Whenever I speak to a group of MSPs, I ask if they have long-term team members they care about deeply and want to help achieve their financial goals. Recently, I asked this question, and nearly every hand in the room went up. However, here’s the reality: if you don’t run a business with a true net profit — after the owner’s salary — of at least 20%, and if you don’t achieve financial independence yourself, you cannot help your people. Think of the advice given on airplanes: secure your own mask first before assisting others.

You cannot give to others what you do not have, no matter how good your intentions. This is why I tell our TruMethods Peer members that building a profitable business isn’t just about you and your personal goals. Every team member, no matter their position in your organization, depends on your success.

This perspective is why I don’t like to see any quarterly “Goose Eggs” from our members. A “Goose Egg” is going an entire quarter without adding a new ogo sale. Consider what a “Goose Egg” could mean for others in your business. Developing this mindset has helped me become a better businessperson throughout my career. It has also led me to connect my company’s growth and profitability directly to my role as a leader and to my self-image.

Shifting to this way of thinking takes effort, but it’s worth it. I’ve learned that most people are more motivated to achieve goals that impact others. While we may let ourselves down occasionally, we work hard not to let others down.

As you plan your life and business goals for 2025 and beyond, I encourage you to adopt this perspective. It could transform not only your business but also your role as a leader.

The Coming MSP Revolution: Why AI Will Fundamentally Reshape Our Industry

Posted on | Author Gary Pica

Over the past few weeks, I’ve had the opportunity to speak with numerous MSPs at our North American and EMEA Peer meetings, as well as Kaseya Connect in Vegas. There’s a lot of optimism in our industry. Everyone seems excited about where things are heading. SMBs, our customers, continue to invest more in technology, and more companies are outsourcing. The growth opportunities feel endless right now. I love it when people have higher expectations.

However, when I ask about the future changes that are coming and how they’ll impact our business model, I feel that people are underestimating the impact of what’s to come. Most of the conversations I’m having suggest leaders are thinking about small adjustments, not the massive shift that’s actually coming. I believe we have experienced an evolution of our business model up until now, and a revolution is on the horizon.

Over the past decade, our industry has evolved. Many MSPs have matured operationally, while the security landscape has changed tools and technology. We’ve weathered economic ups and downs, figured out remote work, and adapted to countless new technologies along the way. These evolutions have resulted in more MSPs becoming larger and more profitable. But through this, the basic structure of an MSP is the same, with support being the foundation of cost and value. We have piled a lot of tools up, but our foundation has remained. Whether it’s RMM, PSA, security tools, or backup solutions, we’ve basically been stacking more stuff on top of the same core business. Your team closes a lot of tickets and deals with a lot of alerts.

Over the next three to five years, advancements in AI and automation will dramatically change what we have known as support. We’re not talking about simple chatbots here—this is AI that can actually diagnose problems and fix complex issues. There will be fewer tickets and alerts, and AI and automation will accomplish an increasing percentage of support noise. Password resets, software installs, network tuning, system maintenance—all of it happening without your techs touching anything. This will be the first fundamental reshuffling of the MSP industry.

I don’t think the leaders I have spoken to over the past few weeks fully realize what this shift will mean to their business and, more importantly, what they need to do to succeed in this transition. The technology is already here, and some MSPs are using it now, which means this is happening faster than most people think.

I’ll discuss more in the future about what you need to do to make the first real revolution in our industry a huge opportunity, but for now, start to think about what your business, your operations, your packaging and pricing, your value proposition—all of it—will look like when support is a small percentage of what it is today.

The MSPs who figure this out early will have a huge advantage over those who wait.