Outreach on Outreach

How to improve sales rep 1:1s with Outreach

Cassie Pless, Sr. Director of Commercial Sales at Outreach's Avatar

Cassie Pless, Sr. Director of Commercial Sales at Outreach

One-on-one meetings between sales managers and reps can build trust and help reps achieve their full potential. With a productive check-in, managers gain insight into their sales reps' activities to help them improve effectiveness, move deals along, and grow in their careers.

But without structure or true visibility into deals to identify addressable risks and improve execution throughout the sales cycle, these meetings can be a waste of time for everyone.

Here, we'll review four keys to having more effective meetings with your reps: 

  • Why 1:1s are important
  • Where sales leaders go wrong in 1:1s
  • How to conduct an effective deal review in 1:1
  • How to help your reps close more deals with Outreach

    Why 1:1s are important

    Regular 1:1s between reps and managers — when done well — not only help reps grow in their career and hone their skills, but provide managers with coaching opportunities to help their team create more pipeline and close more deals.

    These meetings can also lead to improved employee retention and training, and help managers identify people on their team who are best suited to train new reps.

    Where sales leaders go wrong in 1:1 meetings

    With more and more distributed teams, there’s no way managers can know every deal inside and out to forecast accurately (let alone which reps need help where), and trying to do so leads to teams feeling micromanaged instead of supported.

    Many 1:1s rely on standardized questions managers think will help them understand deals and blockages. However, it may be impossible to fully understand risks and opportunities by relying on the same weekly questions.

    And if you’re relying on your team’s “gut feel” on how their deals are going, you may not be getting an accurate — or complete — picture of how the deal is actually progressing.

    Only reliable data indicates deals that could be in jeopardy.

    In the example below, the sales manager may spend their time coaching the wrong deal based on a rep’s gut feel. And the leader also might forecast the wrong numbers when predicting where their sales will land for the month or quarter.

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    When deal review in 1:1s aren’t run effectively due to reliance on anecdotes and gut feeling, deals can become at risk. Sales leaders must be able to help prioritize and focus conversations where they can add the most value. Reps may not always know what to ask to get the coaching they need. A sales leader’s job is to guide reps to the best possible outcomes — which is challenging without the correct data.

    How to conduct an effective deal review in 1:1

    Preparation and consistency are keys to productive 1:1s. Sales managers must seize the chance to help their sellers get better at closing their best opportunities, and these meetings are a perfect place to do it, so long as managers take steps to maximize their face-to-face time with each rep.

    Our top tips to conduct effective deal reviews: 

    1.  Set a schedule (and stick to it)

    For maximum impact — set 1:1s regularly and early in the week — and don’t cancel. Also, keep agendas consistent; block out 45 minutes, with 30 minutes for each meeting, and 15 minutes to reflect and prepare for the next.


    2. Do your homework


    Prep for each meeting by gaining visibility into deals and milestones before the 1:1, so you are familiar with your sales reps’ current deals.

    Prepare a list of data-driven questions and considerations to help you determine which deals need your attention during the meeting:

    • Which deals are at risk or stagnating?
    • Have dollar amounts or close dates changed?
    • How many emails, calls, and meetings have occurred?
    • Is the rep following your ideal sales process?

    3. Collaborate on agendas

    Managers should prepare the right data points to help the rep understand the whole picture and where they need to focus. Encourage your reps to add key questions to the agenda to indicate exactly where they could use a bit more coaching or support.

    4. Separate deal data review from coaching

    Managers should understand deal data beforehand so they can ask fewer fact-finding questions and focus more on coaching to close. This time is an opportunity to learn from reps and use feedback to find ways to unblock their progress, whether that be through adjusting messaging, working with product development, or offering extra support.

    5. Establish expectations and set action items for both parties

    Make 1:1s feel like a purposeful collaboration to move things forward. Use the last 15 minutes to discuss what you want to happen between now and the next meeting, write down your action items, and be accountable to each other.

      How to help your reps close more deals with Outreach

      Using Outreach, managers can better advise their reps throughout the sales cycle, prep for 1:1s, and create meaningful agendas based on true visibility, not assumptions. Outreach Guide — Outreach’s deal management solution — acts as a much-needed assistant for reps, boosting rep efficiency and productivity by eliminating painful non-selling tasks, providing AI-generated insights during sales meetings, and identifying the next best actions throughout the entire sales process.

      Gain transparency into deal health without micromanaging

      Outreach gives an at-a-glance deal health score that reflects the current deal state. It also indicates what’s going well and pinpoints exactly what actions to focus on, to get deals back on track. This way, when you go into a 1:1 with your rep, you’ll already know where their deals stand, steps they’ve taken to close it, and where there’s room for improvement. 

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      Leverage rep sales calls to create teachable moments

      Outreach’s Kaia doubles as an AI-enabled assistant coach and can transcribe entire sales calls while capturing action items and key meeting moments to help reps win. After the call, managers gain visibility into important aspects of the meeting to determine coaching moments for their reps. For example, was pricing discussed with the customer, what objections did the prospect have, and did the rep know how to overcome them? Kaia provides managers an opportunity to avoid micromanaging and coach reps based on real interactions — instead of hypothetical situations.

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      Optimize sales execution with mutual action plans

      Mutual action plans — or what we call Success Plans — allow sellers to reduce deal risk and increase close rates by making sure the right stakeholders are engaged. Success Plans in Outreach helps your reps build buyer trust and alignment to collaborate with relevant internal and external stakeholders throughout the buyer journey. Success Plans also gives managers more transparency into how the deal is progressing and what the seller-buyer relationship looks like.

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      Unlock more time for coaching and more wins for your whole team

      With Outreach, managers spend less time fact-finding and more time coaching. Deal health highlights where to focus so you don’t waste time where it doesn’t make sense. More productive 1:1s also mean more opportunities for training and finding moments to highlight with the larger team.


      With true visibility into your team’s deals, you’ll gain the confidence to guide your reps throughout the selling process. Outreach Guide delivers a collaborative experience that helps sellers and managers improve execution throughout the sales cycle. Schedule a demo today to learn more.