Rob Whitfield - Redefine Winning
@redefinewinning.bsky.social
I help leaders rapidly accelerate and elevate their team’s performance.
Let's be honest; there's a lot of market uncertainty right now.
Here's how we coach leaders to respond:
✅ Strengthen your results and visibility.
✅ Elevate your relationships.
✅ Prepare a plan B just in case you need it.
Book a free strategy call here: www.redefinewinning.com/consultation
Here's how we coach leaders to respond:
✅ Strengthen your results and visibility.
✅ Elevate your relationships.
✅ Prepare a plan B just in case you need it.
Book a free strategy call here: www.redefinewinning.com/consultation
November 12, 2025 at 7:25 PM
Let's be honest; there's a lot of market uncertainty right now.
Here's how we coach leaders to respond:
✅ Strengthen your results and visibility.
✅ Elevate your relationships.
✅ Prepare a plan B just in case you need it.
Book a free strategy call here: www.redefinewinning.com/consultation
Here's how we coach leaders to respond:
✅ Strengthen your results and visibility.
✅ Elevate your relationships.
✅ Prepare a plan B just in case you need it.
Book a free strategy call here: www.redefinewinning.com/consultation
It's hard to do this sometimes, especially with deadlines, that urgent project, and the fire you weren't expecting.
You'll always be busier than the time you have available.
But it's important to keep challenging the status quo so you can achieve your full potential - and...
You'll always be busier than the time you have available.
But it's important to keep challenging the status quo so you can achieve your full potential - and...
November 11, 2025 at 6:40 PM
It's hard to do this sometimes, especially with deadlines, that urgent project, and the fire you weren't expecting.
You'll always be busier than the time you have available.
But it's important to keep challenging the status quo so you can achieve your full potential - and...
You'll always be busier than the time you have available.
But it's important to keep challenging the status quo so you can achieve your full potential - and...
Teams win faster when you recognize different ways people create value: Visionary, Driver, Executor, Team Player, Connector, Analyst.
Name them. Normalize them. Design around them.
Get the full research report now: www.redefinewinning.com/newsletter
Name them. Normalize them. Design around them.
Get the full research report now: www.redefinewinning.com/newsletter
November 10, 2025 at 5:45 PM
Teams win faster when you recognize different ways people create value: Visionary, Driver, Executor, Team Player, Connector, Analyst.
Name them. Normalize them. Design around them.
Get the full research report now: www.redefinewinning.com/newsletter
Name them. Normalize them. Design around them.
Get the full research report now: www.redefinewinning.com/newsletter
Hey, 2026 is under 8 weeks away.
How are you getting on with your work-based resolutions from this year?
We've had an uptick in folks reaching out for coaching that borders on maximizing the value of what they do in their current role/career progression while...
How are you getting on with your work-based resolutions from this year?
We've had an uptick in folks reaching out for coaching that borders on maximizing the value of what they do in their current role/career progression while...
November 7, 2025 at 6:25 PM
Hey, 2026 is under 8 weeks away.
How are you getting on with your work-based resolutions from this year?
We've had an uptick in folks reaching out for coaching that borders on maximizing the value of what they do in their current role/career progression while...
How are you getting on with your work-based resolutions from this year?
We've had an uptick in folks reaching out for coaching that borders on maximizing the value of what they do in their current role/career progression while...
Hiring: Do you have a constant, revolving door of people joining and leaving?
Do you have mixed or poor Glassdoor reviews?
Act now; these issues are already impacting your business outcomes and they'll compound if left unchecked.
Effective leaders know this and they act.
Do you have mixed or poor Glassdoor reviews?
Act now; these issues are already impacting your business outcomes and they'll compound if left unchecked.
Effective leaders know this and they act.
November 6, 2025 at 5:45 PM
Hiring: Do you have a constant, revolving door of people joining and leaving?
Do you have mixed or poor Glassdoor reviews?
Act now; these issues are already impacting your business outcomes and they'll compound if left unchecked.
Effective leaders know this and they act.
Do you have mixed or poor Glassdoor reviews?
Act now; these issues are already impacting your business outcomes and they'll compound if left unchecked.
Effective leaders know this and they act.
Can we talk about how people don't speak up properly in meetings?
People text, chat, or Slack one another in the same room/meeting, or whisper in a surreptitious side bar.
Can we agree that none of these help bring the team together?
Let's agree on a 'no side bar conversations' rule...
People text, chat, or Slack one another in the same room/meeting, or whisper in a surreptitious side bar.
Can we agree that none of these help bring the team together?
Let's agree on a 'no side bar conversations' rule...
November 5, 2025 at 6:45 PM
Can we talk about how people don't speak up properly in meetings?
People text, chat, or Slack one another in the same room/meeting, or whisper in a surreptitious side bar.
Can we agree that none of these help bring the team together?
Let's agree on a 'no side bar conversations' rule...
People text, chat, or Slack one another in the same room/meeting, or whisper in a surreptitious side bar.
Can we agree that none of these help bring the team together?
Let's agree on a 'no side bar conversations' rule...
Align For Strengths. Flex For Gaps. Elevate Results.
Just as individuals have unique love languages for expressing affection, team members have distinct ways of expressing and contributing value at work.
Redefining what it means to win in a team context means appreciating...
Just as individuals have unique love languages for expressing affection, team members have distinct ways of expressing and contributing value at work.
Redefining what it means to win in a team context means appreciating...
November 4, 2025 at 5:50 PM
Align For Strengths. Flex For Gaps. Elevate Results.
Just as individuals have unique love languages for expressing affection, team members have distinct ways of expressing and contributing value at work.
Redefining what it means to win in a team context means appreciating...
Just as individuals have unique love languages for expressing affection, team members have distinct ways of expressing and contributing value at work.
Redefining what it means to win in a team context means appreciating...
We've just completed a research project on team member archetypes.
There are 21 reasons why you need to understand these.
They will enable or inhibit your success.
Sign up now or send a DM and we'll send you the article.
www.redefinewinning.com/newsletter
There are 21 reasons why you need to understand these.
They will enable or inhibit your success.
Sign up now or send a DM and we'll send you the article.
www.redefinewinning.com/newsletter
November 3, 2025 at 5:50 PM
We've just completed a research project on team member archetypes.
There are 21 reasons why you need to understand these.
They will enable or inhibit your success.
Sign up now or send a DM and we'll send you the article.
www.redefinewinning.com/newsletter
There are 21 reasons why you need to understand these.
They will enable or inhibit your success.
Sign up now or send a DM and we'll send you the article.
www.redefinewinning.com/newsletter
Work reality: Same issue every quarter: new deck, same plot.
Spot it: Recurring “war rooms,” calendar creep, projects that never quite die.
Kill the sequel:
1. Institute exit criteria for projects (what “done” means, and who declares it).
Spot it: Recurring “war rooms,” calendar creep, projects that never quite die.
Kill the sequel:
1. Institute exit criteria for projects (what “done” means, and who declares it).
October 31, 2025 at 4:24 PM
Work reality: Same issue every quarter: new deck, same plot.
Spot it: Recurring “war rooms,” calendar creep, projects that never quite die.
Kill the sequel:
1. Institute exit criteria for projects (what “done” means, and who declares it).
Spot it: Recurring “war rooms,” calendar creep, projects that never quite die.
Kill the sequel:
1. Institute exit criteria for projects (what “done” means, and who declares it).
Trope: Boo! You didn’t see it coming.
Work reality: Board asks “How’s adoption?” and we scramble because we track lagging vanity metrics.
Spot it: Beautiful dashboards, zero decisions, retroactive reporting, last-minute data hunts.
Fix it fast:
Work reality: Board asks “How’s adoption?” and we scramble because we track lagging vanity metrics.
Spot it: Beautiful dashboards, zero decisions, retroactive reporting, last-minute data hunts.
Fix it fast:
October 30, 2025 at 4:25 PM
Trope: Boo! You didn’t see it coming.
Work reality: Board asks “How’s adoption?” and we scramble because we track lagging vanity metrics.
Spot it: Beautiful dashboards, zero decisions, retroactive reporting, last-minute data hunts.
Fix it fast:
Work reality: Board asks “How’s adoption?” and we scramble because we track lagging vanity metrics.
Spot it: Beautiful dashboards, zero decisions, retroactive reporting, last-minute data hunts.
Fix it fast:
Work reality: We blame “the market,” but delays come from unclear priorities and missing decision rights.
Spot it: Urgent-everything; leaders escalate by default; teams stall waiting for approval.
Fix it fast:
1. Publish a 1-page priority stack (Now/Next/Later) with explicit trade-offs.
And...
Spot it: Urgent-everything; leaders escalate by default; teams stall waiting for approval.
Fix it fast:
1. Publish a 1-page priority stack (Now/Next/Later) with explicit trade-offs.
And...
October 29, 2025 at 4:45 PM
Work reality: We blame “the market,” but delays come from unclear priorities and missing decision rights.
Spot it: Urgent-everything; leaders escalate by default; teams stall waiting for approval.
Fix it fast:
1. Publish a 1-page priority stack (Now/Next/Later) with explicit trade-offs.
And...
Spot it: Urgent-everything; leaders escalate by default; teams stall waiting for approval.
Fix it fast:
1. Publish a 1-page priority stack (Now/Next/Later) with explicit trade-offs.
And...
Work reality: Functions optimize locally; projects die off-screen.
Spot it: Handoffs > ownership. Competing backlogs. “That’s not our OKR.”
Fix it fast:
1. Appoint a single accountable owner for outcomes across functions.
2. Create a shared mission + 3 measures that everyone owns.
And...
Spot it: Handoffs > ownership. Competing backlogs. “That’s not our OKR.”
Fix it fast:
1. Appoint a single accountable owner for outcomes across functions.
2. Create a shared mission + 3 measures that everyone owns.
And...
October 28, 2025 at 4:55 PM
Work reality: Functions optimize locally; projects die off-screen.
Spot it: Handoffs > ownership. Competing backlogs. “That’s not our OKR.”
Fix it fast:
1. Appoint a single accountable owner for outcomes across functions.
2. Create a shared mission + 3 measures that everyone owns.
And...
Spot it: Handoffs > ownership. Competing backlogs. “That’s not our OKR.”
Fix it fast:
1. Appoint a single accountable owner for outcomes across functions.
2. Create a shared mission + 3 measures that everyone owns.
And...
Welcome to our Hallowe’en series, where classic thriller & horror tropes mirror everyday organizational life.
Over this week, we’ll tackle:
• Don’t split up (silos)
• The call is coming from inside the house (root causes)
• Jump-scare metrics (surprise reporting)
and...
Over this week, we’ll tackle:
• Don’t split up (silos)
• The call is coming from inside the house (root causes)
• Jump-scare metrics (surprise reporting)
and...
October 27, 2025 at 4:45 PM
Welcome to our Hallowe’en series, where classic thriller & horror tropes mirror everyday organizational life.
Over this week, we’ll tackle:
• Don’t split up (silos)
• The call is coming from inside the house (root causes)
• Jump-scare metrics (surprise reporting)
and...
Over this week, we’ll tackle:
• Don’t split up (silos)
• The call is coming from inside the house (root causes)
• Jump-scare metrics (surprise reporting)
and...
Whatever your role, whatever your focus, have you considered how you'll de-risk your role and team for the next 18 months?
Most people answer, "no." Give how busy we all are, it's not a surprise.
But it's a big miss that leaves a lot of personal and professional value on the table.
Most people answer, "no." Give how busy we all are, it's not a surprise.
But it's a big miss that leaves a lot of personal and professional value on the table.
October 24, 2025 at 5:50 PM
Whatever your role, whatever your focus, have you considered how you'll de-risk your role and team for the next 18 months?
Most people answer, "no." Give how busy we all are, it's not a surprise.
But it's a big miss that leaves a lot of personal and professional value on the table.
Most people answer, "no." Give how busy we all are, it's not a surprise.
But it's a big miss that leaves a lot of personal and professional value on the table.
We're seeing an uptick in inquiries from executives, leaders, and team members about resilience - both at the individual and team levels.
With everything happening in the world right now, it's unsurprising.
Survival is now the new sustainability; we're all judged on our ability to protect margins
With everything happening in the world right now, it's unsurprising.
Survival is now the new sustainability; we're all judged on our ability to protect margins
October 23, 2025 at 5:25 PM
We're seeing an uptick in inquiries from executives, leaders, and team members about resilience - both at the individual and team levels.
With everything happening in the world right now, it's unsurprising.
Survival is now the new sustainability; we're all judged on our ability to protect margins
With everything happening in the world right now, it's unsurprising.
Survival is now the new sustainability; we're all judged on our ability to protect margins
What's your leadership style?
Go on, describe it.
Hopefully you shared that it depends on the context, people involved, and emotions involved.
The most successful leaders flex their style based on these, and other, factors.
But honestly, we ask people in sessions and they've...
Go on, describe it.
Hopefully you shared that it depends on the context, people involved, and emotions involved.
The most successful leaders flex their style based on these, and other, factors.
But honestly, we ask people in sessions and they've...
October 22, 2025 at 4:50 PM
What's your leadership style?
Go on, describe it.
Hopefully you shared that it depends on the context, people involved, and emotions involved.
The most successful leaders flex their style based on these, and other, factors.
But honestly, we ask people in sessions and they've...
Go on, describe it.
Hopefully you shared that it depends on the context, people involved, and emotions involved.
The most successful leaders flex their style based on these, and other, factors.
But honestly, we ask people in sessions and they've...
"Workslop" - part 2. It's not harmless. Here's why;
Cost signal: estimated productivity loss ≈ $186 per employee/month; reputational hit too; recipients view senders as less creative, capable, and reliable.
Organizational drag: the burden shifts downstream; receivers must interpret, correct...
Cost signal: estimated productivity loss ≈ $186 per employee/month; reputational hit too; recipients view senders as less creative, capable, and reliable.
Organizational drag: the burden shifts downstream; receivers must interpret, correct...
October 21, 2025 at 4:50 PM
"Workslop" - part 2. It's not harmless. Here's why;
Cost signal: estimated productivity loss ≈ $186 per employee/month; reputational hit too; recipients view senders as less creative, capable, and reliable.
Organizational drag: the burden shifts downstream; receivers must interpret, correct...
Cost signal: estimated productivity loss ≈ $186 per employee/month; reputational hit too; recipients view senders as less creative, capable, and reliable.
Organizational drag: the burden shifts downstream; receivers must interpret, correct...
We know that AI will be a part of our work future, as much as the internet will be. However, are you seeing an increase in, “Workslop”?
What is it? Polished-looking but shallow AI output (memos, decks, emails) that creates extra work for others rather than progress.
About 40% of U.S. desk workers
What is it? Polished-looking but shallow AI output (memos, decks, emails) that creates extra work for others rather than progress.
About 40% of U.S. desk workers
October 20, 2025 at 5:15 PM
We know that AI will be a part of our work future, as much as the internet will be. However, are you seeing an increase in, “Workslop”?
What is it? Polished-looking but shallow AI output (memos, decks, emails) that creates extra work for others rather than progress.
About 40% of U.S. desk workers
What is it? Polished-looking but shallow AI output (memos, decks, emails) that creates extra work for others rather than progress.
About 40% of U.S. desk workers
If I asked you whether you contribute to your organization's success, I'm sure you'd answer, yes.
Most people consider what they do when reflecting on the answer. They'll have a long list of actions taken.
The smarter approach is to consider how you contribute.
There are 4 stages of contribution
Most people consider what they do when reflecting on the answer. They'll have a long list of actions taken.
The smarter approach is to consider how you contribute.
There are 4 stages of contribution
October 17, 2025 at 4:07 PM
If I asked you whether you contribute to your organization's success, I'm sure you'd answer, yes.
Most people consider what they do when reflecting on the answer. They'll have a long list of actions taken.
The smarter approach is to consider how you contribute.
There are 4 stages of contribution
Most people consider what they do when reflecting on the answer. They'll have a long list of actions taken.
The smarter approach is to consider how you contribute.
There are 4 stages of contribution
Welcome back to part two of our Workplace Polarization series.
Here are 4 leader moves to reduce polarization (fast).
1. Practice self-awareness. Know your triggers; share them to humanize the room.
2. Reward courage, not conformity. Incentivize thoughtful dissent and actively seek...
Here are 4 leader moves to reduce polarization (fast).
1. Practice self-awareness. Know your triggers; share them to humanize the room.
2. Reward courage, not conformity. Incentivize thoughtful dissent and actively seek...
October 16, 2025 at 4:25 PM
Welcome back to part two of our Workplace Polarization series.
Here are 4 leader moves to reduce polarization (fast).
1. Practice self-awareness. Know your triggers; share them to humanize the room.
2. Reward courage, not conformity. Incentivize thoughtful dissent and actively seek...
Here are 4 leader moves to reduce polarization (fast).
1. Practice self-awareness. Know your triggers; share them to humanize the room.
2. Reward courage, not conformity. Incentivize thoughtful dissent and actively seek...
Let's be clear; workplace polarization ≠ “different opinions.”
Instead, it's what happens when constructive dialogue collapses and people cluster into like-minded camps that keep reinforcing their own beliefs. That’s when trust erodes and teams go tribal.
A hidden driver? The illusion that...
Instead, it's what happens when constructive dialogue collapses and people cluster into like-minded camps that keep reinforcing their own beliefs. That’s when trust erodes and teams go tribal.
A hidden driver? The illusion that...
October 15, 2025 at 5:25 PM
Let's be clear; workplace polarization ≠ “different opinions.”
Instead, it's what happens when constructive dialogue collapses and people cluster into like-minded camps that keep reinforcing their own beliefs. That’s when trust erodes and teams go tribal.
A hidden driver? The illusion that...
Instead, it's what happens when constructive dialogue collapses and people cluster into like-minded camps that keep reinforcing their own beliefs. That’s when trust erodes and teams go tribal.
A hidden driver? The illusion that...
Part 2 of 2: Intentionality over speed:
Principle #1: Redefine responsiveness: praise thoughtful contributions over instant replies; make “substance over speed” explicit in reviews/meetings.
Principle #2: Make expectations explicit: no after-hours reply pressure; move updates to an async tool;
Principle #1: Redefine responsiveness: praise thoughtful contributions over instant replies; make “substance over speed” explicit in reviews/meetings.
Principle #2: Make expectations explicit: no after-hours reply pressure; move updates to an async tool;
October 14, 2025 at 3:50 PM
Part 2 of 2: Intentionality over speed:
Principle #1: Redefine responsiveness: praise thoughtful contributions over instant replies; make “substance over speed” explicit in reviews/meetings.
Principle #2: Make expectations explicit: no after-hours reply pressure; move updates to an async tool;
Principle #1: Redefine responsiveness: praise thoughtful contributions over instant replies; make “substance over speed” explicit in reviews/meetings.
Principle #2: Make expectations explicit: no after-hours reply pressure; move updates to an async tool;
“Urgency culture” rewards reactivity over results; people look busy, but impact drops.
Constant responsiveness kills deep work; decisions get faster but worse, and burnout rises while high performers disengage.
And nobody cares if you're working for the 15th hour today. In fact, it likely...
Constant responsiveness kills deep work; decisions get faster but worse, and burnout rises while high performers disengage.
And nobody cares if you're working for the 15th hour today. In fact, it likely...
October 13, 2025 at 4:40 PM
“Urgency culture” rewards reactivity over results; people look busy, but impact drops.
Constant responsiveness kills deep work; decisions get faster but worse, and burnout rises while high performers disengage.
And nobody cares if you're working for the 15th hour today. In fact, it likely...
Constant responsiveness kills deep work; decisions get faster but worse, and burnout rises while high performers disengage.
And nobody cares if you're working for the 15th hour today. In fact, it likely...
Redefining winning sometimes means pausing.
A hospital visit last week forced me to act like the leader I coach others to be: set boundaries, trust the team, let the system run.
They delivered.
Clients noticed the outcomes, not my absence.
A hospital visit last week forced me to act like the leader I coach others to be: set boundaries, trust the team, let the system run.
They delivered.
Clients noticed the outcomes, not my absence.
October 10, 2025 at 5:50 PM
Redefining winning sometimes means pausing.
A hospital visit last week forced me to act like the leader I coach others to be: set boundaries, trust the team, let the system run.
They delivered.
Clients noticed the outcomes, not my absence.
A hospital visit last week forced me to act like the leader I coach others to be: set boundaries, trust the team, let the system run.
They delivered.
Clients noticed the outcomes, not my absence.
Part 2 of 2 on RTO insights:
Where we're heading is just as important as where we've been. AI talent is pushing back on RTO; AI roles are ~3× more likely to be remote, and Head-of-AI roles are surging.
If leadership resists enabling remote, it’s a red flag (reactive leadership or financial strain)
Where we're heading is just as important as where we've been. AI talent is pushing back on RTO; AI roles are ~3× more likely to be remote, and Head-of-AI roles are surging.
If leadership resists enabling remote, it’s a red flag (reactive leadership or financial strain)
October 9, 2025 at 4:45 PM
Part 2 of 2 on RTO insights:
Where we're heading is just as important as where we've been. AI talent is pushing back on RTO; AI roles are ~3× more likely to be remote, and Head-of-AI roles are surging.
If leadership resists enabling remote, it’s a red flag (reactive leadership or financial strain)
Where we're heading is just as important as where we've been. AI talent is pushing back on RTO; AI roles are ~3× more likely to be remote, and Head-of-AI roles are surging.
If leadership resists enabling remote, it’s a red flag (reactive leadership or financial strain)