Growth Mindset Episode - Drive Strategic Decision-Making by Asking Smarter Questions

In this Growth Mindset Episode, Danny dives deep into the essentials every new manager needs to thrive: Strategic Thinking, Talent Management, and Delegation. Packed with insights from the Harvard Business Review and some of Danny's favorite reads, this video is a masterclass in modern leadership.

🚀 What You'll Learn:

How to ask the right questions to drive smart decisions.
The secrets to managing freelancers and full-time employees in today's dynamic workforce.
Proven techniques to delegate effectively and empower your team.
Danny also shares real-world examples from the cybersecurity field and reflects on leadership lessons from top books like Think Again by Adam Grant and Creativity, Inc. by Ed Catmull.

Whether you're stepping into management for the first time or looking to sharpen your leadership skills, this episode has something for you.

🔗 Join the conversation, enhance your leadership toolkit, and elevate your career. Don’t forget to like, subscribe, and share if you find value in the content!

Catch the full episode now and transform the way you lead! 🎧💼

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Guest Drink Appearance by  @guayaki   Organic Yerba Mate - Orange Exuberance

Chapters

• 0:00 Growth Mindset Episode #3
• 0:29 Article #1: The Art of Asking Smarter Questions
• 1:17 The First Question - Investigative
• 1:43 The Second Question - Speculative
• 1:58 The Third Question - Productive
• 2:22 The Fourth Question - Interpretive
• 2:51 The Fifth Question - Subjective
• 3:06 Running Through an Example
• 5:56 Article #2 - Talent Management
• 6:50 Initial Question - Why Does it Seem there are more Freelancers now?
• 8:20 New Blended Approach #1 - Culture
• 8:40 New Blended Approach #2 - Institutional Knowledge
• 9:10 New Blended Approach #3 - Digital Workloads
• 9:29 New Blended Approach #4 - Communication
• 10:05 Article #3 - Delegating
• 11:42 Tool #1 - Mindset
• 12:06 Tool #2 - Identify Strenghts and Weaknesses
• 12:53 Tool #3 - Communication
• 13:47 Tool #4 - Milestone Check-Ins
• 14:09 Tool #5 - Final Review

Transcript

[00:00:00] Danny: Hey, welcome back to the show. In this growth mindset episode, we're going to be talking about three topics. Strategic thinking, talent management, and delegating as a first time manager. I have my yerba mate, orange exuberance, let's do this. 


Article #1: The Art of Asking Smarter Questions
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[00:00:29] Danny: So the first article from Harvard Business Review is entitled, The Art of Asking Smarter Questions. These five techniques can drive great strategic decision making. So the situation. Organizations are facing increased urgency and uncertainty in this day and age. They need the ability to start asking smarter questions but lack formal training.

So why is this so challenging? Manager's expertise often blinds them to new ideas. Your professional success and deep experience may actually affect your problem solving ideas. More on this later. The article provides a remedy by asking strategic questions grouped into five domains. 


The First Question - Investigative
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[00:01:17] Danny: The first, investigative, what's known. You need to ask yourself what you or your team want to achieve and what you need to learn to do so. Imagine you're explaining something to a kid and they keep on asking you, why, why, why? It's exactly the same thing, but less annoying. This technique helps you dig deeper and not stop at superficial answers.


The Second Question - Speculative
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[00:01:43] Danny: The second one, speculative or what if? Speculative questions help you consider the problem more broadly. This helps us overcome limiting assumptions and jump starting that creative problem solving.


The Third Question - Productive 
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[00:01:58] Danny: The third one Now what? By asking, how can we get it done? How will we measure progress? This helps you identify key metrics and develop milestones and potential bottlenecks. This is where strong program management skills and great communication skills will keep you moving forward. 


The Fourth Question - Interpretive
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[00:02:22] Danny: The fourth one, interpretive. Or, so what? Think of this as something Sense making questions. It enables you to continually redefine the core issues to go beneath the surface and ask, what is this problem really about? These types of questions provide the momentum to move from one mode of inquiry to another, and they convert information into actionable insights. 


The Fifth Question - Subjective
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[00:02:51] Danny: And the last one is subjective. What's unsaid? This is all about looking outward, and how will we make sense of our new service or product? You need to take the emotional aspect into account. 


Running Through an Example
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[00:03:06] Danny: Let's take a look at an example I created through a set of questions within the context of cybersecurity and specifically ransomware. So we take investigative questions. What happens if ransomware continues? Number two, speculate. What opportunities or risks do we need to be concerned about when it comes to ransomware? Productive. What does that imply for scaling up our defenses? Interpretive. Why are ransomware attacks so frequent? What are we as defenders doing that is increasing or decreasing ransomware? Subjective. If we are impacted by ransomware, will our customers and people's personal lives be affected? In other words, have we done our due diligence and care, and can it be measured? Ultimately, you want to balance your set of questions and determine your style of inquiry.

And something that really got me thinking about this article our are two books. The first one is Think Again by Adam Grant, where he talks about tapping into the power of knowing and what you don't know. He wants us to rethink and unlearn what we've learned. Sounds a little bit like Yoda.

He categorizes people into three personas. First, the preacher who defends their most powerful beliefs. The prosecutor who proves the other side is wrong. This is definitely happening all over this country. And the last one, the politician who is campaigning for approval of our cherished beliefs.

He proposes that we need to be more like a scientist who are searching for the truth. I'm just at the beginning of the book, but it has similar concepts to this article. The second book is something I've been talking about a lot on LinkedIn. Creativity, Inc. by Ed Catmull.

In the chapter called Hidden, Ed talks about how smart people or companies do stupid things. We can cite hubris, short term solutions, but Ed posits that the problem is deeper than that. Leaders were not attuned to the fact that there were problems they could not see. They were not aware of blind spots, and they assumed that problems did not exist.

Again, something very similar to this article. We need to be more inquisitive and go beyond the superficial questions and be more like scientists collecting data. In the end, you need to explore critical areas with a diverse team so you can surface key information, insights, and options you might otherwise have missed.


Article #2 - Talent Management
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[00:05:56] Danny: The second article is about talent management. The article is titled, Highly Skilled Professionals Want Your Work, But Not Your Job. Freelancers, are in huge demand today, and they know it. It's time for new rules of engagement. This article really resonated with me because cybersecurity job market is extremely tough and believe it's contracting.

During the past year, I've met Dozens of people that are choosing to go the freelancer route. The challenge. With the influx of freelancers choosing to be their own bosses, companies are struggling to recruit and retain top talent. Implications. A new model is developing where you're mixing in house or full time employees with freelance talent into an interesting hybrid.


Initial Question - Why Does it Seem there are more Freelancers now?
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[00:06:50] Danny: Managers need to be cognizant of how to manage these disparate groups. But first, I have a question. Why are freelancers more prevalent now, or at least it seems like they are? It could be the economy, tough job market could be playing a part. But more flexibility, short bursts of high intensity work, and then period of tranquility.

But the ability to work anywhere, as long as the need is there, is very attractive for some. And I would argue freelancers also like the autonomy, the variety of different roles. They can work on a three month contract and pivot to something else totally different. Tell me when the last time you were able to do that working at your company. 

So how do managers effectively lead within this new dynamic work? How do you get freelancers to embrace the culture like their full time employees? Or is that even a requirement? What are freelancers roles and responsibilities during a crisis? Will full time team members feel annoyed when they don't contribute during crisis mode? I would argue you can't manage it in the same way as temp or contract workers who are typically hired for staff augmentation. Freelancers are hired to drive innovation or advisory services based on their skill set and experience.


New Blended Approach #1 - Culture
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[00:08:20] Danny: So the article talks about a new blended approach. First thing is provide the same culture training to everyone. I don't know how I feel about this. You're paying for their time. And if the freelancer is there for less than six months, I personally believe you're wasting money on that cultural training.


New Blended Approach #2 - Institutional Knowledge
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[00:08:40] Danny: Number two, keep all institutional knowledge in house. The last thing you want is an experienced, skilled professional delivering on a key project and then leaving without passing that knowledge down to the full time employees or part of your team. To mitigate this, you have to have your full time employees shadow them and be co participants of the deliverables. Again, you must put that in the contract, otherwise it might be an issue down the road.


New Blended Approach #3 - Digital Workloads
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[00:09:10] Danny: Manage digital workflows. Freelancers are typically juggling multiple clients, therefore you need to build mutual trust that they will do everything the contract requires them to do. Therefore, keep good digital workflows with milestones. It's essential to keep the project on schedule.


New Blended Approach #4 - Communication
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[00:09:29] Danny: Lastly, you need to overly communicate both from the manager side and from the freelancer side. A downside of freelance work is the lack of employee benefits, according to this article.

But the new generation might be using their voting power to create an alternative to the employee sponsored model that we've had for probably a generation. Overall, this article is understanding the dynamic of a diverse team and juggling the best approach to make sure you're able to get all the innovation from your freelancers without affecting your full time employees or staff.


Article #3 - Delegating
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[00:10:05] Danny: The last article is learning to delegate as a first time manager. And let me tell you, I love this article and really resonated with me because I've experienced it but I've seen it around the different roles that I've had both as new leaders and even seasoned leaders still having a hard time delegating. Or managers having a hard time delegating. So, here's the situation. Picture your first time leading a team. You were given several projects from your manager and now you need to deliver them in a timely manner to showcase your team's value. Did you find yourself overwhelmed because you were doing the majority of the tasks?

You're not alone. First time managers struggle because they are trying to find the balance of them doing the work and delegating the work. So why is this so challenging? Prior to being promoted, managers were more than likely great individual contributors. And this is kind of my personal opinion. If you're a great individual contributor, That doesn't necessarily translate into being a good manager and then even a higher level being a great leader.

However, when you become a manager, you must shed your individual contributor mindset, easier said than done, and adopt a new one. The key is delegating and building trust within the team. It might sound counterintuitive, but the higher you advance in the career ladder, the less you'd be involved in from a day to day project based work.


Tool #1 - Mindset
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[00:11:42] Danny: So, the article provides five tools for you to navigate this transition. The first tool is changing your mindset. Again, very hard to do. But you must understand that you're now managing and not doing the day to day work. You're providing your team all the necessary training, tools, and expertise they need to be successful. You're providing your team all the necessary training, tools, And expertise They need to be successful.


Tool #2 - Identify Strenghts and Weaknesses
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[00:12:06] Danny: Number two, once you've changed your mindset, you need to determine what to delegate and to whom. You need to identify your team's strengths and weaknesses to help them add value to the team's mission and overall organizations. So this could be as an example, SWOT analysis, strength, weaknesses, opportunities, and threats.

But there are some questions that you can ask. What project or task can I delegate so I can focus on a high level, strategic based projects? What project can be a learning opportunity for my team to develop? And lastly, can portions of this project be better suited to someone's strengths? This is all about understanding your individual team members strengths and weaknesses.


Tool #3 - Communication
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[00:12:53] Danny: The next one, clearly communicate the task or project to your individual team members and make sure you clarify roles and next steps. What does success look like? Identify the interdependencies, the key stakeholders, what team are you going to be collaborating all of this has to be identified and conveyed to the individual or the team leading this project. You're laying the foundation for the project and providing clear and concise instructions.

So what you can do is set up a meeting to explain all of this. This is also a great opportunity for them to ask you questions, to make sure they understand the task at hand. And maybe you don't let them go until they start asking questions. Maybe you can talk about asking more strategic questions, being inquisitive, being speculative, and all of that.


Tool #4 - Milestone Check-Ins
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[00:13:47] Danny: And then lastly, when you do develop milestones and you're in for a check in, you want to provide that feedback. So during the milestone check in, provide feedback, especially if they were able to meet the milestone. Again, use this as an opportunity to elicit questions and give them that positive feedback.


Tool #5 - Final Review
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[00:14:09] Danny: And lastly, you just want to review and reflect after the project is done. You need to provide feedback and have candor and identify the weaknesses, but frame it in a way that it's not going to belittle them. It's not going to shame them. But failure is a good thing. And I know that might be hard to really understand or even grasp, but when failure happens in a, I guess I would argue maybe just in, in office standpoint or in a work environment, if failure happens and doesn't hurt anybody, it doesn't harm anyone. But If it happens in a welcoming environment, then the individual who failed or the team that failed is going to learn so much more.

That concludes this episode. Thank you again for watching. If you liked this video, please hit the like button, subscribe, and share. If you have ideas for future growth mindset episodes, please reach out. Maybe I can start dissecting podcasts or books that I've read. The next guest episode will be in two weeks. You can watch or listen on YouTube or your favorite podcast platforms. Until next time