Marty Osborn on intentional leadership, shared rewards, and letting a team grow.

Osborn traces his career through software businesses, including Datastream, before starting his own company with a business partner. The company helped organizations implement software for maintaining facilities, equipment, and other assets. He describes the goal as getting the software working, helping people adopt it, and supporting the customer’s operational goals.

His motivation also involved the kind of workplace he wanted to create. Osborn recalls writing a personal manifesto after becoming frustrated with corporate leadership. The central idea was caring about employees, customers, and the problem itself.

That last point matters when choosing what to build or sell. A founder can become attached to a particular solution and stop asking whether it addresses the customer’s difficulty. Osborn’s interest was in implementation projects succeeding. That gave the company a reason to keep examining how it worked, beyond simply delivering a piece of software.

Osborn asks leaders to consider what people say about them after they leave the room. Employees can describe a dismissive boss or a supportive manager without consulting a mission statement. Those descriptions reveal the behavior people actually encounter.

He wanted the company’s leadership to choose those qualities deliberately and practice them consistently. A claim about caring for people means little when a manager gets angry, ignores input, or makes every decision about themselves. A leader’s personal habits need to support the organization’s stated values.

The team eventually had to make its expectations more explicit. After parting ways with a senior person who did not fit the culture, colleagues could recognize the mismatch but struggled to define it clearly. That experience helped them turn assumptions into language they could use in hiring and management.

Osborn says early hiring decisions created some of his largest mistakes. He sometimes became excited about a candidate without fully considering how that person would contribute to the broader team. Training someone and then discovering a poor fit cost time as well as money.

The company’s process eventually involved fifteen interviews. Osborn presents that as the process his team developed, giving candidates and colleagues many opportunities to understand one another. The final stage included a thirty-minute presentation to a group on a subject the candidate chose, which let the team observe communication under pressure.

The useful lesson extends beyond the number of interviews. Hiring should reveal how someone listens, communicates, and works with the people they will join. Osborn also learned to let his team own the process, instead of allowing his enthusiasm as the founder to dominate the decision.

The discussion spends substantial time on two assessment frameworks the company used: DISC and Working Genius. Osborn explains how these gave colleagues a shared language for discussing decisions, communication, and work preferences.

With DISC, he describes his own tendency to make decisions quickly and seek interaction. His business partner preferred more detail. A proposal that Osborn found frustrating could be work his partner was better suited to examine. Posting profiles made those differences easier to discuss when deciding how to communicate.

Working Genius helped the team talk about stages of work, including generating ideas, judging them, encouraging action, supporting others, and finishing. Osborn describes a colleague who enjoyed completing a task list, and another who kept modifying sales presentations because he enjoyed creating something new.

These are examples of how this team used the frameworks, rather than proof that an assessment determines someone’s abilities. The practical habit was asking why a task energized one person and frustrated another. That question sometimes turned an apparent personal disagreement into a conversation about how the work was assigned.

A conversation with fellow entrepreneur Scott Millwood challenged Osborn’s approach to growth. Osborn had been asking operational questions while keeping his hands in many parts of the business. Millwood told him that his own involvement was the problem.

Osborn describes the uncomfortable period that followed. At times he sat in his office resisting the urge to call a customer or step into work someone else now owned. Letting go challenged his sense of usefulness, even though it gave colleagues space to do their jobs.

He says the company performed better as he relinquished control. His advice to his younger self would be to make that change sooner. For founders, the account identifies a common obstacle: responsibility can move on an organization chart while the founder continues to reclaim it through everyday interventions.

Osborn credits a leadership event with helping him see the business more clearly. He and his partner attended an EntreLeadership summit covering the practical work of running a company. He returned ready to set a more ambitious direction, including a goal to double the business over three years.

The team then spent several days together using Patrick Lencioni’s The Advantage to work through the organization’s mission, vision, and values. Osborn connects the value of that time with learning more about colleagues as people.

Understanding someone’s history can change how a team interprets their behavior. Osborn argues that closer relationships helped the leaders commit to a shared direction. He also describes staying through company events because he wanted to spend time with employees, instead of making a brief ceremonial appearance.

Caring about people included recognizing when the leader’s convenience created work for someone else. Osborn describes a rule against sending routine emails over the weekend. Even a message that says a response can wait can interrupt an employee’s time with family.

His alternative was to write the message when convenient and schedule it to arrive during the working week. That preserves the sender’s ability to clear their thoughts without transferring the burden immediately.

The point is concrete: employees respond to what leaders do, including notification times. A stated commitment to balance needs support from ordinary communication decisions. Being interested in colleagues’ lives also means giving them time to live those lives.

Osborn disliked reward trips reserved for a small group of top performers. The company instead set a company target twenty percent above the previous year’s number. If the company reached it, everyone would go to the Caribbean; if it missed the goal, nobody would.

He recalls the company passing the target in August and says the trips helped employees and their families build relationships. The company also included students in its cooperative education program. Osborn believes that experience encouraged students to tell classmates about the company and supported recruitment.

The example shows how a reward can communicate who belongs. Including employees across roles and students made the trip consistent with the team identity Osborn wanted to build.

His closing answer returns to intentionality. If sales are down, hiring another salesperson is one possible response. He suggests examining the underlying problem first: the team may need training, a better process, or outside coaching. The same discipline applies to culture. Decide what a practice should accomplish, then consider what employees will actually experience.