CEO and co-founder at Wunder Fund — high frequency trading firm.
In our fast-paced business climate, founders and managers often view recurring one-on-one meetings as just another task competing for their limited time. However, implemented intentionally, I’ve found that regular monthly check-ins with team members can provide immense value for the entire organization.
At my company, we’ve developed a system for monthly one-on-ones that I’ve found to yield productive, engaging discussions that drive tangible outcomes. I’d like to share this strategy for productive check-ins with you.
The Foundation: A Discussion Template
Preparation is key. Before each meeting, I recommend that you have your employees complete a simple template that provides the framework for your conversation. Sections prompt reflection and updates on:
Goals
• What have you succeeded in? What did you do well? What are you proud of?
• What failures have you encountered? What are you not proud of?
• What can you do to prevent these failures from recurring?
Updates
• Latest KPIs.
• What new information have you received from the world? What have you learned?
• What tasks have drained your energy this month, and which ones gave you energy?
Issues • What tools are you missing to achieve your goals? What do you need but don’t have?
Feedback
• What have you liked about my actions or the company’s actions in general?
• What would you like to change in my actions, the company’s actions, or the organization of processes?
• What else should we do that we are not currently doing, in your opinion?
This consistent structure creates space for meaningful dialogue on all aspects of the employee’s growth and performance as well as overarching organizational health.
The Mindset: Radical Candor
With the template’s guidance in place, I think you will find that a mindset shift will occur. As a manager, you should consciously cultivate radical candor, including honest, caring communication. Employees should know they can surface concerns, critiques and suggestions without judgment. As a part of this, commit to addressing issues quickly and clearly.
I strive to draw out constructive feedback—especially negative input. This unvarnished truth is invaluable for identifying problems early, removing blockers and enhancing processes. Make sure to thank team members for sharing pushback and aim for positive resolutions.
Execution: Making Every Minute Count
Armed with the template’s insights, you can dedicate your time to what matters most. Employees receive coaching tailored to their needs and priorities, and you gain a more accurate pulse on your team’s abilities, motivations, pain points and goals. Misalignments tend to get realigned.
After each monthly round of one-on-ones, I feel reconnected to my team’s needs and aspirations. And employees feel heard, valued and supported. As trust builds, conversations become increasingly candid and productive.
The Competitive Advantage
In today’s war for talent, these regular touchpoints demonstrate a real commitment to professional development and unlocking each person’s potential. Thoughtfully implemented one-on-ones can allow you to know your team deeply as individuals and optimize their engagement and growth.
Yes, monthly one-on-ones demand an investment of time, but the payoff is immense: enhanced manager-employee relationships, solving of problems/blockers, retention of top talent, personalized support and ultimately, greater individual and organizational performance.
Tips For Success
To maximize the value of monthly one-on-ones, keep these tips in mind.
• Set a consistent cadence for meetings to maintain momentum.
• Block 30 to 60 minutes to allow substantive discussion.
• Have employees complete templates in advance to guide the conversation.
• Focus on listening to understand, not just reply.
• Thank employees for feedback and follow up on action items.
• If major issues emerge, schedule additional time.
• After meetings, reflect on key insights gained.
The Bottom Line
Implemented with care, these recurring conversations build trust, transparency and individual growth. They demonstrate that employees are valued partners, not just workers on an assembly line.
Of course, this protocol requires an initial level of candor and security. At the same time, regular one-on-one meetings act as a positive feedback loop. With each new meeting, I think you’ll find that your interaction with the employee will become increasingly transparent and honest.
By maintaining open lines of communication and focusing on both individual and company goals, you can work together to maximize productivity.
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