The Check-In Question of Check-In Questions
What you can learn from it, what is required and what if it's not for you
How you check in with your team in the workplace matters more than you think.
Recently, a LinkedIn post addressed this point, including offering one bold question.
A check-in question is “… a structured way to get grounded in a meeting setting and acknowledge we all show up to work — to meetings — differently, every day, in a unique way,” wrote Bernhard Kowatsch, the head of innovation accelerator at the UN World Food Programme.
One of the more interesting ones that Kowatsch presented was extremely direct yet open ended.
“If today was your last day... " was listed as an advanced-level question to consider.
”But isn’t that just an icebreaker?” Kowatsch rhetorically asked. “It sometimes is a sort of that, but a good check-in question allows people to give actual insights into how they are doing, their state of mind…. and contributes to a more diverse, open and safe meeting environment.”
Leaders however may not feel confident presenting it to their people because they don’t know how it will be experienced, perceived and judged.
“This question cuts to the core of people’s personal reflections, which may feel uncomfortable in a work setting,” says Amy Spurling, the founder and CEO at Compt, a platform that helps companies create personalized employee benefits through Lifestyle Spending Accounts (LSAs).
“To ask this effectively, leaders need to create an environment of psychological safety well before the meeting. This means consistently building trust, modeling vulnerability and reinforcing that there are no 'wrong' answers.”
Spurling offers a suggestion for bringing up the question with more effectiveness.
“Leaders should also set the stage by framing the question not as a philosophical or existential challenge but as an opportunity for team members to reflect on what matters most to them,” she says.
“A good way to start is by answering the question yourself first, honestly and thoughtfully,” Spurling says. “If you model transparency and openness, your team will be more inclined to do the same.”
If a member of the organization can come to feel safe replying, important findings could be discovered, which might, in some manner, benefit leaders and organizations.
“This question has the potential to reveal what truly motivates and matters to employees beyond their work tasks,” Spurling says. “It can help leaders understand their team's priorities, values and what gives them a sense of purpose.
“For example, if multiple people mention spending time with loved ones, it may indicate a need for more work-life balance or stronger mental-health support within the organization.”
Learning not only brings knowledge, which can help improve subsequent actions.
“When leaders have clear insights into employee well-being and engagement, they're able to make better decisions around policies that foster fulfillment, belonging and overall satisfaction,” Spurling says.
“It’s also a reminder that work should be meaningful and aligned with individual values, which is something that organizations can build upon to create a stronger culture of purpose.”
There remains uncertainty though in inquiring “If today was your last day…”
“There is a real risk in asking this question if the culture isn't already one of openness and trust,” Spurling says. “If the environment isn't psychologically safe, employees may feel pressured to respond inauthentically or be uncomfortable with sharing personal details in a professional setting.”
She elaborates.
“It may also not be the right question for everyone. Some employees might find it too intense or simply not relevant to their current mindset, which could detract from the overall goal of the check-in,” Spurling reasons. “It's important to know your people and how they might respond to the question before asking it.”
Yet for those who favor or are intrigued by the question and want to move forward with it, Spurling reiterates its value.
“But, when asked in a trusting environment, the question can deepen relationships, encourage reflection and allow people to show up as their whole selves at work,” she says.
“Whatever question you ask your team, it's important to demonstrate that, as a leader, you care about more than just output: you care about your people’s values, emotions, and what matters to them in life. This creates a stronger, more engaged team.”
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