strategy session

Jessica, mid-level employee, sat at her desk, staring at a growing to-do list and an inbox full of unanswered emails. Her frustration wasn’t just about the workload; it was about the lack of direction. She felt disconnected from her manager, unsure if her efforts aligned with the team's priorities. She had tried to initiate one-on-one meetings to clarify her goals, but her manager always seemed unprepared or distracted. Jessica worried her career was stagnating, and her upcoming performance review loomed over her like a dark cloud.

Then she decided to try something different. Instead of asking for another generic check-in, Jessica approached her manager and said, “Hey, can we have a strategy session?” The response was immediate. Her manager’s eyes lit up with interest, and they scheduled a dedicated hour later that week. Little did Jessica know, this simple shift in language would transform not only her relationship with her boss but also her career trajectory.

The term “strategy session” holds power. Unlike vague requests for a “1:1” or a “check-in,” it signals intentionality and alignment. Most managers juggle competing priorities and dread meetings that lack a clear purpose. By framing the conversation around strategy, you’re tapping into your manager’s mindset of planning and action, making them more likely to engage meaningfully.

Here’s why this approach works:

To ensure a productive meeting, preparation is key. Here’s how you can take charge of the conversation:

2. Align with team goals:
Review your team’s objectives and think about how your contributions fit into the bigger picture. Be ready to discuss how your work supports overall priorities.

3. Draft an agenda:
Include topics like:

4. Gather data:
Bring examples of your achievements, challenges, and areas where you need support. Be ready to back up your points with metrics or specific anecdotes.

When the strategy session begins, set the tone with clear communication and actionable steps. Here’s a framework you can follow:

To maximize the impact, don’t let strategy sessions be a one-time event. Incorporate them into your routine by:

Strategy sessions aren’t just about day-to-day alignment; they also set the stage for successful performance reviews. By proactively discussing your goals, progress, and challenges, you demonstrate ownership of your career and make it easier for your manager to advocate for you. These sessions create a narrative of consistent growth and alignment, which can lead to better evaluations and opportunities for advancement.

Jessica’s decision to ask for a strategy session not only clarified her goals but also strengthened her relationship with her manager. She felt more confident, focused, and motivated—and her manager appreciated her proactive approach. By adopting this simple yet effective strategy, you too can take control of your career, ensure alignment with your team, and set yourself up for success. Start today by asking, “Hey, can we have a strategy session?” and watch how it transforms your professional journey.

Effective communication is the most paramount element to success for every team. It is crucial for expectations and responsibilities to be clearly communicated and understood for goals to be met. However, managers frequently fail to communicate effectively. Without clear communication, teams often feel confused and frustrated and have demonstrated decreased productivity throughout groups. Poor communication can appear in a variety of mediums, including unclear instructions or responsibility expectations leading to repeated work or missed deadlines. When communication issues go unaddressed, they can contribute to an unhealthy work environment, hindering productivity and achievement and fostering a negative culture. 

The consequences of poor communication can be very impactful to a team. Group members experiencing communication issues commonly feel aggravated, unengaged, or confused, which all lead to an overall decrease in efficiency, team-wide. Another significant problem with poor communication is the elimination of critical feedback that is necessary for growth and improvement. Without proper feedback, employees may struggle to improve their performance or coordinate effectively with their team members.

For direct reports, initiating a conversation about communication challenges can be a daunting task. But, poor communicators will not realize their ineffectiveness unless someone brings it to their attention. Many employees fear that bringing up an issue such as this with a director may be viewed as criticism rather than constructive feedback. To avoid this issue, direct reports should phrase the meeting as a strategy session to talk about effective communication methods for the team. Rather than presenting flaws and personal attacks, direct reports should present solutions for the issues the team experiences, without pointing fingers. Fostering an open and honest conversation about communication gaps is essential for improving team culture and is a cornerstone to improving productivity. 

Prior to addressing communication concerns with superiors, direct reports need to recognize and document the specific issues affecting the team. Poor communication can happen through any medium but identifying the root of the issues will help in creating a strategy to improve. Some common indicators of ineffective communication are vague or confusing instructions, last-minute changes, and inconsistent messaging, creating a lack of transparency across a team. Perhaps most notably, managers will realize there has been a communication failure when a deadline or important deliverable is missed or inadequate. 

When discussing potential improvements with a leader, direct reports should be sure to come up with specific examples and targeted solutions. Rather than making ambiguous or vague statements, team members should really bring light to the problems the team has experienced with concrete examples of the patterns observed. Pointing out these issues with appropriate solutions aids in the manager's understanding of how an action may be affecting their team. 

By clearly explaining the problems and offering some solutions, a collaborative approach to problem-solving can be achieved to improve communication habits. When discussing potential solutions, direct reports should consider any tool that could benefit the group or team. When struggling with communication, team members may offer a variety of solutions including scheduling consistent check-in meetings, sending meeting recap emails, utilizing goal-tracking software, or holding open brainstorming sessions. By narrowing the focus to specific issues with proactive solution possibilities, team members can assist team leaders in building a beneficial communication environment. 

By pinpointing communication gaps, offering constructive feedback, and open communication methods, employees are enabled to improve the overall working environment of their team. Through proactive communication, direct reports can help lead the team to become a highly productive and collaborative group. 

Although many communication issues can stem from a team leader or manager, it is also the group members' responsibility to uphold a beneficial communication culture within their team. To find sustainable changes for a team, members should work to build a communication norm of open and honest communication. Creating a norm of open communication dialogue will enable managers to share feedback and areas of improvement better, improving the skills of team members. 

The most crucial step to fostering open communication is establishing repeating opportunities for providing feedback. Leaders should be open to hearing what their direct reports have to say, whether, in questions or suggestions for new ideas, both parties grow from giving and receiving feedback. Managers who prioritize psychological safety within their teams will see the most success in creating an open dialogue within their teams. Creating a safe space where team members feel empowered to learn from each other and embrace mistakes will enable further conversation and collective growth. Although the onus may be on the manager to set the tone, it is the team's responsibility to consistently contribute and engage in communication to foster a positive culture. 

Overcoming previous communication issues to rebuild a positive communication norm within a team can be challenging. Oftentimes a poor tone at the top can influence the entire team to shift to ineffective communication. Team members and direct reports struggling with the manager's communication should recall that it is likely, not intentional. A difficult factor of communicating is that leaders who are poor communicators usually will only find out at the failure or collapse of a project or effort. Managers are commonly unaware of how their communication style and habits will impact the team. By finding specific examples of miscommunications, matching the resulting impact, and suggesting targeted solutions, members of a team can contribute to improving a communication issue. 

Effective communication is essential for every team but can be a common struggle for leaders. Miscommunication can create frustration, confusion and can deteriorate the productivity within a team as well. Direct reports play a vital role in bringing communication issues to light with their superiors and finding targeted solutions to approach communication flaws. Beyond individual conversations, direct reports have a key responsibility to uphold and practice positive communication habits and foster a productive team environment. Through proactive planning and innovative thinking, communication issues can be overcome to build a strong, collaborative, and efficient team culture. 

Emily was a top performer. As an operations specialist at a fast-growing tech firm, she had spent three years mastering her role, streamlining processes, and consistently exceeding performance metrics. But despite her clear qualifications and aspirations for growth, her manager, Dan, continued to stall her promotion. It wasn’t that Dan didn’t recognize her talent; he depended on it. The thought of replacing Emily, training someone new, and potentially losing productivity made him hesitant to let her advance.

This situation is more common than employees might think. A manager may not consciously sabotage an employee’s growth, but their reluctance to let go of a high-performing team member can create an invisible career ceiling. The challenge for employees like Emily is navigating this bottleneck strategically, ensuring they don’t remain stuck in a role that’s too convenient for management to change. 

From Dan’s point of view, Emily was a linchpin in the team’s success. She handled high-priority tasks with precision, trained new hires, and solved problems before they escalated. Promoting her meant finding someone equally competent, training them, and accepting a potential period of reduced efficiency—all of which felt like unnecessary risks.

However, this mindset can be detrimental to both the employee and the organization. Companies that fail to promote from within risk losing top talent, damaging morale, and sending a message that growth opportunities are limited. For Dan, he needs to be sure about how to evaluate whether someone is ready for a promotion as well. Emily knew she had to approach the situation with both patience and a strategic plan.

Emily understood that directly confronting Dan about his reluctance would not be effective. Instead, she needed to frame the conversation in a way that addressed his concerns while advocating for her own growth. Here’s how employees in a similar situation can navigate this discussion:

Rather than jumping straight into why she deserved a promotion, Emily started by recognizing Dan’s perspective. She acknowledged that she understood how valuable she was to the team and expressed appreciation for the opportunities she had been given.

Instead of making it about personal growth alone, Emily highlighted how her promotion would ultimately benefit the company. She emphasized that stepping into a leadership role would allow her to:

To alleviate Dan’s fears about losing her expertise, Emily presented a plan outlining how she could gradually transition her responsibilities to a successor. This included training a replacement, documenting key workflows, and ensuring continuity in her absence.

Emily then asked Dan directly: “What steps do you see as necessary for me to move into a leadership role?” By shifting the conversation toward actionable SMART goals, she encouraged Dan to define what he needed to see from her before approving a promotion.

To prevent the conversation from becoming an indefinite discussion, Emily worked with Dan to set a timeline for reevaluating her promotion. They established measurable benchmarks and agreed to revisit the conversation within three months to track progress. 

Instead of assuming her manager’s intent, Emily scheduled a one-on-one strategy session with Dan. This wasn’t just a casual career check-in—it was a structured conversation with a clear agenda:

One of Dan’s biggest concerns was replacing Emily. To ease this, she proactively began training a junior colleague, documenting workflows, and suggesting a transition plan. By demonstrating that her team wouldn’t suffer in her absence, she removed one of Dan’s key barriers to promoting her.

Emily also recognized that promotions often require advocacy from more than just a direct manager. She began increasing her visibility within the company by:

This approach ensured that multiple decision-makers recognized her readiness for advancement.

Rather than positioning the conversation as a personal request, Emily framed her promotion as a strategic move for the company. She highlighted how moving into a leadership role would allow her to drive greater impact, mentor others, and enhance team efficiency.

This reframing helped Dan see the long-term benefits rather than focusing on the short-term inconvenience.

To avoid endless delays, Emily and Dan agreed on a clear timeline for revisiting the promotion decision. They set a three-month period to track progress against defined objectives. This ensured accountability and kept the conversation from becoming an indefinite cycle of “maybe later.”

Employees like Emily must recognize their manager’s concerns while advocating for their own growth. By aligning on expectations, developing a transition plan, and framing the promotion as a win-win, they can shift the conversation from reluctance to action. Ultimately, career advancement isn’t just about proving capability; it’s about making it easy for decision-makers to say yes.