I had just been hired on in a senior strategic marketing role in an industry new to me, and job one was acclimating to the market and industry dynamics and trying to understand what a customer looked like in this world.

After the obligatory round of meetings with company executives, division heads and as many of their team members as I could convince to allocate some time, I recognized that the context, while appreciated, lacked the depth you can only gain from connecting with customers and industry players on their home turf.  No rocket science here, just good common sense.

The sales and customer teams were happy to schedule some client meetings with me, and I appreciated their courtesy, but I wanted to go about this in a different manner.

The typical “new executive wants to meet customers” meetings (or, as I’ve heard them referenced, “educate the idiot from corporate” meetings) many of us have attended or at least witnessed, are largely ceremonial and usually highly caloric. Long lunches or factory tours followed by fancy dinners are lousy ways to do anything other than waste everyone’s time and expand your waistline. I suggested an alternative.

I asked for the opportunity to ride-along/travel with the firm’s top sales representative from each region. I wanted to gain my insights through the windshield and eyes of the people out finding and serving clients and partners. I had the good fortune to be working with a sales executive who understood that the better educated I was, the better I could work with and serve his team. And to ensure that I was in for the full experience, he set me up with two week long trips…Sunday night to Friday.

5 Valuable Lessons You Learn Riding with a Great Sales Professional:

1. Success knows no shortcuts. There is no down time. Waking hours are working hours. From planning time over breakfast to strategizing in parking lots to setting up the next few days activities during the evenings. The only thing that a sales representative has to invest is time, and the best ones invest this time wisely.

2. Follow the money after you understand the real problems. You need to know both the people with the budgets and the people with the problems. We met with plenty of decision-makers on our tour, usually after spending considerable time with the people doing the work and feeling the pain points.

3. The best way in to a new client is usually not through the front door. When we found ourselves with rare time between scheduled meetings, I learned a few lessons in people skills and chutzpah as this rep pulled into a gated parking lot after saying out loud, “I’ve been meaning to get into this firm for awhile. Let’s try it.” He proceeded to talk our way through the guard gate. Instead of heading in the front door, we started at the docks and ended up eventually finding the person with the right title for a 30-minute introduction meeting. This person was so impressed with the creativity of getting in to see him, he agreed to give us time at his team’s monthly meeting. While security measures may have tightened since he employed that approach, the lesson was very real.

4. It’s impossible to know what’s really going on in a game from the skybox seats. After weeks of listening to glowing reports of all of the great things my new company was doing (and why competitors were flummoxed in the process), it was painfully clear that the market reality didn’t match the corporate messaging. Warts, bumps, bruises, bruised egos, the emotions from the customers and alliance partners impacted by the programs, and the true strengths of competitors suddenly became much clearer after talking with the people using and selling our systems.

5. After riding with a rep, your view on supporting the front-line team members will never be the same. Spend a few weeks total riding or travelling with your top representatives, and in spite of the early awkwardness, you will form an important bond with these individuals, and you will cultivate a level of empathy for the challenges of everyone in that role that will make you a better professional.

The Bottom-Line for Now:

I recognize that not everyone has the latitude to “ride with a rep.”  However, you can foster relationships and seek out the insights and wisdom of the people carrying the bags and cultivating the clients.  Find ways to provide help to the people in the field and show genuine interest in learning from and supporting these professionals, and they will repay you with insights and observations you can only learn in the trenches.

For those who come into senior roles, you will likely have the opportunity to gain access to clients and other staff members. Say “no thanks” to the ceremonial and mostly superficial client meetings at this level, and roll up your sleeves and help carry the bags for your top producers for a few days. The education is priceless.