Frequency and Timing of Fieldwork

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Fieldwork is a game-changer in sales management. Getting out there with your reps, meeting clients face-to-face, and seeing the action up close can make all the difference. But here’s the big question: how often should you be in the field with your team? And when’s the best time to do it?

Too much fieldwork can pull you away from strategic planning and back-office tasks. Too little, and you lose touch with what’s really happening on the ground. Let’s break down how to find that perfect balance in frequency and timing of fieldwork, so you stay connected without feeling stretched thin.

Why Fieldwork Matters

Fieldwork isn’t just a “nice to have” — it’s essential. By being in the field with your reps, you get a firsthand look at their strengths, weaknesses, and overall approach. It’s one thing to read about their progress on a CRM dashboard; it’s another to see them in action.

Imagine you’re in the field with Sarah, one of your top reps. You notice she’s excellent at building rapport, but when it comes to handling objections, she sometimes falters. This is something you might not catch if you’re only looking at the numbers. Being there lets you see these moments, step in with coaching, and give Sarah the specific support she needs to improve.

Fieldwork keeps you in the loop and helps you give tailored feedback that can transform your team’s performance.

How Often Should You Do Fieldwork?

Now, onto the big question: how often should you be out there with your team? The answer depends on a few factors: your team size, the complexity of the sales cycle, and your reps’ experience levels.

Here’s a general guide to help you decide:

  1. For Newer Reps: Aim for more frequent field visits—around once a week, if possible. New reps need more hands-on guidance, and fieldwork is your chance to show them the ropes. It’s also a confidence booster for them, knowing you’re there to support them directly.
  2. For Experienced Reps: Less frequent visits, like once or twice a month, might be enough. Experienced reps don’t need as much hand-holding, but regular check-ins help you stay connected and catch any bad habits that may have slipped in over time.
  3. For High-Priority Accounts or Big Deals: Be flexible here. If a rep has a major deal coming up, consider being there regardless of the usual schedule. High-stakes calls are a great opportunity for you to offer extra support and see how your rep handles pressure.

Timing: When’s the Best Time to Join?

Timing can be everything. To get the most out of fieldwork, think about what stage the client is at and what your presence will add. Here are some times when it makes sense to join your reps:

  1. Early in the Relationship: If your rep is meeting a new client for the first time, your presence can add credibility. Plus, it’s a chance to make a solid first impression and set the tone for a long-term partnership.
  2. During Key Points in the Sales Cycle: For example, if the client has raised serious objections, or if it’s time for a product demo, your presence can be incredibly helpful. You can provide guidance, answer questions directly, and help steer the conversation if things get challenging.
  3. For Follow-Ups and Check-Ins with Important Clients: It’s not just about closing deals. Being there for follow-up meetings shows clients that you’re invested in their success, not just their initial purchase. It’s also a great way to reinforce relationships and keep tabs on satisfaction.

Structuring Your Fieldwork: Making Each Visit Count

Fieldwork shouldn’t be about just “showing up.” To make the most of your time in the field, here’s a simple framework you can follow:

1. Pre-Call Planning

Before the visit, sit down with your rep to go over the goals for the call. What’s the objective? What are the likely objections? What’s the ideal outcome? This isn’t just about prepping the rep; it’s also about aligning on how you’ll handle the meeting together.

For example, if the goal is to close a deal, you might decide that the rep leads the conversation while you step in only to handle tough questions. Having a plan keeps the call focused and avoids any “stepping on toes” moments.

2. Observation and Coaching During the Call

During the call, be a supportive observer. Let your rep take the lead and show their skills. Step in only if needed. Pay close attention to how they handle objections, build rapport, and present the product. These moments are golden opportunities to observe and gather insights for later coaching.

If something unexpected happens, stay calm and guide the conversation as needed. Remember, you’re there to back them up—not to take over.

3. Post-Call Debriefing

After the call, debrief right away. This is where the magic happens. Ask the rep what they thought went well and what they’d improve. Offer your feedback, focusing on both strengths and areas for improvement.

For example, if they handled objections well but missed a chance to upsell, point that out. Keep it constructive, specific, and actionable so they leave the debrief with clear steps to improve.

Consistency is Key

Whatever schedule and timing you choose, consistency matters. Fieldwork isn’t a “do it once” kind of thing. Regular, predictable field visits build trust with your team. They know when to expect you, they get used to your coaching style, and they start to see the benefits in their own performance.

Over time, consistent fieldwork creates a culture of improvement. Your team knows that you’re there to help them grow, not just to check boxes. And that’s huge for morale and motivation.

The Bottom Line

Finding the right frequency and timing for fieldwork is all about balance. Too much, and you risk neglecting other priorities; too little, and you lose touch with the team. The sweet spot is somewhere in the middle—enough to stay engaged, without micromanaging.

Fieldwork is your chance to lead by example, to build stronger relationships with clients, and to coach your reps in real-time. So, map out a schedule, stay consistent, and make each field visit count. With the right rhythm, you’ll see your team improve, your client relationships deepen, and your sales numbers climb.

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Peter Strauss

Peter Strauss is an experienced founder with a tech background who’s spent most of his career in sales and marketing, sharing insights along the way.