Coaching in Chaos

In today’s fast-paced and often chaotic environment, effective coaching and leadership are more important than ever. Leaders must have the skills to navigate through uncertainty, adapt to changing circumstances, and still effectively mentor their teams.

In this blog, we pulled together the best lessons from the recent live session with Matt Green, Sam McKenna, Todd Caponi, and Jen Allen-Knuth – as they discuss the critical aspects of Coaching in Chaos. They explore key areas including proactive management, team engagement, restructuring calendars to prioritize tasks, and mentoring early-career professionals in a remote workforce. The discussion provides insights into how leaders can promote visibility, encourage ownership, and foster growth among team members, even in a remote setup. 

So, whether you’re a frontline manager, a seasoned leader, or an early-career professional seeking growth, there are valuable takeaways for everyone. Join us as we explore these insightful strategies and provide practical advice on how to thrive and drive success in the midst of chaos.

Frameworks for Effective Revenue Leadership

It’s crucial for leaders to effectively coach their teams. This involves not only understanding the changing landscape of sales but also harnessing key principles for motivating and managing a sales team.

The 5 F’s of Revenue Leadership

Todd Caponi explained the “Five Fs of Building Revenue Capacity” as a framework that can help new managers, especially those in sales, understand their responsibilities and structure their meetings effectively. Here’s what each of the “Five Fs” represents:

1. Focus: This refers to ensuring that sales representatives spend their most valuable asset – their time – on the right opportunities, people, and prerequisites. As a manager, you can help direct your team’s focus to the areas that are most likely to yield results.
2. Field (Organization): This relates to building the team with the right tools and resources. Managers should ensure their team members have what they need to be successful. This might mean investing in sales enablement tools, training, or additional resources to help the team achieve their goals.
3. Fundamentals: This F emphasizes the importance of getting the basic things right consistently. The fundamentals in sales might include messaging, positioning, understanding the buyer’s journey, negotiation skills, presenting, and demoing. Managers should reinforce these key areas through training and regular feedback.
4. Forecast: As a revenue leader, a manager is responsible for predicting future sales outcomes. This involves maintaining and analyzing sales forecasts, as well as keeping track of key performance indicators (KPIs) to measure and track team performance over time.
5. Fun (Culture): This last F represents the importance of creating an enjoyable, supportive, and engaging work culture. While it might seem less directly tied to sales, a positive and fun work culture can contribute to employee satisfaction, retention, and overall performance. As a manager, fostering this type of environment might involve team-building activities, encouraging open communication, and recognizing and celebrating team successes.

Overall, the “Five Fs” serve as a comprehensive guide for managers, helping them understand and prioritize their responsibilities in leading a successful sales team. Use this model as the structure for your 1:1’s for your team. Create a Google Doc and have a place for you and your team member to add to each one of these categories throughout the week. This minimizes distractions throughout the week and ensures you are making the most of your time together.

The PRAISE Model

Diving a bit more deeply into the Fun & Culture aspect, Todd Caponi described the PRAISE model as a tool to help leaders understand what motivates and engages their employees on an intrinsic level. It’s often difficult to develop a culture in a remote environment, which is why it’s so critical to get down to the intrinsic reason people are motivated to engage. Here’s a breakdown of what each letter stands for:

1. P – Predictability: This refers to the human need for structure and understanding of what’s going to happen next. Employees perform better when they have clear expectations and can predict the outcomes of their actions. This might include clear job descriptions, well-defined roles and responsibilities, and consistent feedback.
2. R – Recognition: Recognition is about acknowledging and validating employees’ efforts and achievements. This can be in the form of public acknowledgment in team meetings, personalized feedback, or rewards for meeting certain performance goals.
3. A – Aim: This speaks to the purpose or “why” behind a person’s work. Employees are often more motivated and engaged when they understand how their work contributes to the larger mission of the company, to their customers, and even to society at large. Leaders can support this by communicating the company’s mission and values and regularly connecting individual work to these larger goals.
4. I – Independence: Trust and autonomy are key to employee satisfaction. People generally perform better when they are given the resources, tools, and freedom to do their jobs without being micromanaged. Leaders can foster this by setting clear expectations and then trusting employees to meet them in their own way.
5. S – Security: This refers to a sense of safety and belonging in a team or organization. Employees who feel secure are more likely to take risks, be creative, and feel committed to their work. This can be fostered through a positive work environment, inclusive practices, and strong, supportive relationships within the team.
6. E – Equitability: Equitability refers to fairness in treatment, opportunities, and compensation within the organization. Employees want to know that the “juice is worth the squeeze”, meaning the effort they put into their work is fairly rewarded. Leaders can foster this by being transparent about decision-making processes, pay scales, and advancement opportunities, and ensuring that policies are applied consistently to all employees.

Overall, the PRAISE model is a guide for leaders to think about the key elements that contribute to employee motivation and engagement, especially in a remote or distributed work environment.

As the sales landscape continues to evolve and challenges arise, keeping sales reps motivated is critical. By understanding and implementing these principles, sales leaders can ensure they’re coaching their teams effectively and creating an environment conducive to success.

Managing Remote Sales Teams

When coaching a team in a remote environment, the initial step is to set clear expectations. It’s important to understand and communicate that remote work doesn’t follow a strict ‘all-or-nothing’ approach. Organizations may have varying degrees of remote work ranging from fully remote to hybrid models. Defining this up front helps set a baseline for work arrangements, performance measurements, and communication methods.

Setting expectations also involves defining responsibilities and deliverables for each team member. Leaders should regularly discuss individual and team goals, reinforcing the path to achieving them. Moreover, managers need to make themselves available and approachable despite the physical distance. This visible leadership helps in fostering a sense of connectivity and reduces feelings of isolation among remote team members.

Importance of Communication and Collaboration

In remote teams, the frequency and quality of communication directly impact team productivity and morale. Open, regular, and transparent communication becomes the lifeline of remote operations. Managers should make it a point to keep their teams updated about company news, changes, or any relevant information. Not doing so might lead to increased anxiety and uncertainty among team members, impacting their performance negatively.

Collaboration extends beyond the day-to-day tasks. Leaders should involve their teams in setting Key Performance Indicators (KPIs) and goals. This collaborative approach ensures that the team members feel a sense of ownership and engagement toward the company’s objectives. It also helps to align individual and team goals with the broader organizational goals, promoting a unified direction in remote work scenarios.

Transparency and Stability

Transparency is crucial in leading remote teams. It’s essential for leaders to share information about the company’s health, future plans, and any potential challenges with their teams. Doing so reduces fear and speculation, promoting trust and stability. Regularly scheduled updates can offer a consistent feedback loop, providing team members with a sense of certainty even in uncertain times.

Stability in a remote work environment comes from careful planning and wise resource allocation. Leaders who can assure their teams of job security despite external circumstances can cultivate a sense of security and loyalty. This may involve showcasing the financial health of the company, demonstrating that the company can sustain salaries even if no additional closures are made in the short term.

As a leader, you want to encourage and foster this same transparency from your team members. One of the best ways to foster transparency from your teams is based on what you reward. For example, many sales leaders reward verbally pipeline volume. It’s frustrating for reps that are accurately forecasting to see others praised for a pipeline that will never close. Instead, shift your focus on celebrating accurate forecasting. A culture that values realistic, achievable goals over inflated promises can lead to better overall performance and morale. This practice supports transparency, honesty, and accuracy within the team.

Mentorship and Growth in a Remote Workforce

In the era of remote and hybrid work, early-career professionals may struggle to be seen and recognized. However, visibility in a remote work environment isn’t just about physical presence; it is about the individual’s efforts to stand out and make a contribution. 

Making yourself visible involves taking initiatives such as contributing to team meetings and participating actively. For instance, if there is an opportunity to speak or a topic to be discussed, put yourself forward and bring up ideas or solutions you’ve been working on. It’s also important to utilize tools like Slack channels to offer help, give accolades to others, and share your accomplishments in a strategic and non-bragging manner.

When it comes to mentorship, be proactive in reaching out to people you admire. Rather than asking them to be your mentor outright, express your desire to learn from them. Be prepared, do your homework, and make the most out of your time with them. After the meeting, put into practice what you’ve learned and share your progress with your mentor. This shows that you value their time and are serious about growing.

And if you’re a leader managing younger team members, encourage a sense of ownership in individuals seeking to grow in their careers. This includes actively seeking mentorship and advice. Leaders, in return, should be open to their team members seeking mentorship outside their immediate team. They need to understand that the value gained from external mentorship outweighs the potential risk of losing talent.

The aim of these pointers is to create an environment that values recognition, sets clear expectations, and promotes consistency. Monetary rewards are not the sole motivator, and recognition can play an equally important role in motivation. The setting of clear expectations and consistency is even more critical in a remote work environment. Lastly, leaders need to be held accountable for their promises and commitments, creating a more trusting and respectful work atmosphere.

Effective Pipeline Generation Strategies

The desire to generate a pipeline quickly can often result in a flurry of meetings, leading to the misconception that being busy equates to being productive. Instead, it’s crucial to focus on the quality of conversations held with potential clients rather than the quantity of meetings. Here are some ways in which you can foster your reps to build a pipeline in the current environment.

The Power of Self-Sourcing

A common yet surprising gap in many sales departments is the lack of metrics around self-sourcing pipelines. Consistent success in sales can often be attributed to representatives who don’t rely solely on inbound leads or marketing efforts, but instead, take control of their own quotas.

By thinking about sales targets and working backwards from there, representatives can determine what they need to achieve in terms of conversions and average contract value. This process places them at the helm of their own success.

A practical approach is for sales representatives to self-source at least three meetings per week. Whether these meetings involve existing clients or potential new ones within the company, the goal is to generate 3 meetings that can lead to 2 demos and then 1 opportunity. Although challenging, striving for this metric keeps the momentum going and ensures the sales pipeline remains active.

Revamping Pipeline Generation Metrics

Companies often base their pipeline needs on their average win rates. For example, if a win rate is 33%, they aim for a pipeline that is three times their quota. A more cautious and arguably more effective approach is to assume a win rate of 20%. This leads to maintaining a pipeline that is five times the quota, a target that may seem daunting but can lead to fruitful outcomes.

This method not only facilitates better relationships with clients – by eliminating the need to rush deals – but also increases the chances of hitting accelerators if multiple deals close simultaneously.

Smart Pipeline Building

Traditional methods of pipeline building often involve relying on existing networks or the “spray and pray” approach. However, there are smarter and potentially more effective sources. These include reviewing lost deals from the past 18 months, reaching out to people who have changed jobs, or connecting with individuals who used to work at your company and are now part of your territory.

One overlooked strategy is asking your best customers for introductions to their previous employers. This approach leverages existing relationships and can open doors to potential clients.

Building Relevancy With Your Buyers

Salespeople must be part of the learning conversation that potential customers are already having. Observing conversations among potential customers in spaces like LinkedIn or industry conferences can provide crucial insights.

Sales representatives can understand what potential customers care about and ensure their own discussions are relevant. This approach requires learning about the topics potential customers are interested in and linking these back to the solutions your company provides.

Additionally, one often overlooked resource in generating sales lies right within your organization – your colleagues. Particularly those who mirror the persona of your target buyer. This simple approach can provide unique insights that can prove invaluable for your sales strategies.

For instance, if your target buyers are marketers, your internal marketing team can be a valuable resource for understanding their mindset. Regular interactions with them, asking questions about their current focus areas, their performance metrics, and their resources for knowledge, can significantly improve your understanding of your buyer.

This internal resource is not limited to marketing. Depending on who your target buyers are, there will be relevant teams within your organization – finance, operations, IT, HR, etc. By tapping into these internal resources, you can gain valuable insights and refine your selling approach.

An interesting yet frequently overlooked strategy is to review their email inbox (with their permission of course). This process can provide firsthand insights into what catches their attention, what they ignore, what makes them laugh, or which messages they tend to open. These insights can help you design more effective communication strategies that will resonate with your target audience. 

To sum up, building a robust and effective sales pipeline is about more than just the numbers. It involves proactive self-sourcing, thoughtful metrics, maintaining high motivation, smart pipeline building, and engaging effectively with potential customers. It’s about learning from potential buyers and ensuring relevance in every interaction.

Empathy for Decision-Makers, and the Art of Unstalling Deals

Half the battle is won in pipeline generation. However, the more significant challenge often emerges when deals stall. It’s worth noting that the main cause for such stalled deals is not usually competition or pricing, but rather, the clients’ decision that they could either improve their team’s training or choose not to.

The first step to tackling this issue is returning to your initial conversation. By doing so, you can determine if the mistake was on your end or if there was a change in circumstances midway through the deal. If you find that you were overenthusiastic at the early stages and neglected to understand potential obstacles, it’s essential to acknowledge this error.

An honest conversation with your clients can help rectify such situations. Leading with transparency, vulnerability, and authenticity can promote similar behavior from your clients. It’s not about persuading them, but about gaining a better understanding of their needs and barriers.

If the deal got stuck halfway, the objective is to create an environment where they can communicate the truth to you comfortably. Make your assumptions clear and ask for their feedback. This approach encourages transparency and allows you to deal with any unpleasant news appropriately. It’s often the case that deals are lost because the buyer finds it difficult to express their true feelings due to an overzealous attempt to convince them to meet a sales target.

Additionally, you need to ensure that you remain relevant during the sales conversations. Just like your priorities are changing rapidly, your customers have changing priorities. Understanding what your buyers care about is critical to staying relevant. Your value propositions, emails, communications, demos, all should reflect this understanding. 

For instance, consider what success looks like for your buyer. What are their measures of success? How do they aim to get promoted, or earn a raise? By understanding these aspirations, you can tailor your conversations to align with their goals.

Often, sales communications revolve around the features or benefits of the product or service without considering its relevance to the buyer. Such communications tend to lose their effectiveness. So ensure every conversation ties back directly to the performance metrics that matter to your buyers.

It’s important to remember that even when you’re ignored or a deal is labeled as ‘closed, lost’, there’s still a chance for recovery. By communicating openly and providing a comfortable channel for them to respond, such as an asynchronous survey, you might gather insights that could help revive the deal. Sometimes, it’s as simple as realizing that the timing wasn’t right initially but could be more favorable in the future.

When looking back at stalled deals, it’s crucial to consider what might have been overlooked in the previous stages. Conducting strategic deal reviews and asking uncomfortable questions can pave the path to future success. This exercise of asking for feedback is equally vital when applying for jobs and not getting them. While not everyone will provide the feedback you seek, when you do receive it, it offers an invaluable learning opportunity.

Lastly, the role of empathy in your dealings cannot be underestimated. Decision-makers you’re selling to have numerous priorities, and they can only concentrate on a few at a time. The decision to choose one over the other is triggered by predictability and the evaluation of whether the perceived reward is worth the effort. Sometimes, stalled deals result from the buyer’s inability to predict the outcome. By assisting them in this prediction process and demonstrating why your solution deserves to be a priority, you enhance your chances of closing the deal.

Restructuring Your Calendar

If you examine your role as a leader, one of the most illuminating insights you may find is how much of your time is consumed by other people’s priorities. This realization is key to recognizing a significant problem that many leaders face. Whether you’re a president or a frontline manager, your calendar is likely filled with tasks and meetings that cater to others’ needs more than your own.

Recognizing this issue is the first crucial step. Look at your calendar and identify how much of your week is devoted to other people’s priorities versus your own. The next step is addressing the problem and making a change. If your priorities align with motivating your team, coaching to specific KPIs, or fostering engagement within your team, your calendar should reflect that.

The solution involves restructuring your calendar to fit your identified priorities. It’s about embracing actions we know to be beneficial but often overlook, such as declining meetings that are not relevant to us or blocking out enough time for our priorities. Once you realize the reality of your time allocation and start taking action to modify it, you’re likely to witness a significant improvement.

On declining meetings, it’s a humbling exercise to acknowledge that your presence is not always essential for decision-making. Sometimes, the best way to drive the business forward is by focusing on other tasks that align more closely with your priorities. Learning to say, “It seems like all the right people are here. I’m not needed for this meeting, so you can proceed without me,” is a crucial part of calendar restructuring and better prioritization.

Get Started Today

As we’ve explored through these insightful discussions, coaching in chaotic times requires flexibility, resilience, and a deep understanding of team dynamics. These principles stand as the backbone for navigating the turbulent waters of our modern, hybrid work environments. The importance of effective leadership is highlighted now more than ever, with the need for proactive management, fostering team engagement, mentorship, and celebrating wins both big and small.

While we’ve covered a lot, the journey toward becoming an effective leader in chaos is a continual learning process. It’s about adaptation, innovation, and maintaining an unwavering commitment to the growth of your team and your organization, even in the face of adversity. 

As we wrap up this blog, we hope the insights and experiences shared have provided you with actionable strategies and sparked thoughtful introspection on your leadership style. However, nothing beats being a part of the conversation live.

With that in mind, we invite you to join us for our next live session where we will continue to delve into more relevant topics, offer guidance, and share experiences that can help you lead effectively in your professional sphere. Register now and secure your spot to be a part of the live conversation.

Lastly, if you take nothing else away from this blog, know that if you aren’t leading with clarity and transparency right now, your reps are waking up every day unsure of what their future holds. And your team needs a transparent, clear leader. Watch the short clip below and give your reps the clarity they need.