The Weekly Shufflepass - David DeWolf

The Weekly Shufflepass Episode #001: Finding Clarity of Mind

The Weekly Shufflepass is a series of short podcasts in which I talk about something that’s on my mind. They are quick tidbits. No frills. No production. Just helpful thoughts on how you can go, do something greater than yourself.

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My goals during my end-of-year holiday break were to dive in and be with my family and to have a comprehensive planning session that gave me clarity for 2015.

Those two things worked wonders together. I’ve never spent so much time with my family and dove in so much over the holidays. It was refreshing.

That time also gave me perspective and a free mind. It let me let go of all those things going on in the business and let go of all the anxiety and put the to-do items to the side.

Clarity of mind isn’t just about knowing what you’re trying to accomplish. It’s also getting the other muck out of the way.

Here are my strategies for 2015 to focus on clarity of mind. I’ve already seen it work!

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top posts of 2014 - David DeWolf

My Top 12 Posts of 2014

Happy New Year!

What better way to start the New Year than a look back on the highlights of 2014? Here are my most popular posts from the past year.

5 Tips for Getting Your Husband Home from Work

Originally published on November 11, 2013

Most wives are looking for more time with their husband, and many husbands get caught up with work. I bit a controversial topic and got quite a bit of community interaction.

4 Guidelines For Asking Out My Daughter

Originally published on September 15, 2013

There must not be much great content about dealing with your daughter and their dates, because this one ranks #1 on Google for “asking out my daughter.”

3 Tips For Controlling Email So It Doesn’t Control You

Originally published on September 17, 2013

Don’t we all have this problem? So many are constantly looking for solutions.

Why Strategy’s So Important

Originally published on October 25, 2013

Because strategy is so important!

It’s not about getting the right people on the bus

Originally published on December 20, 2011

A classic quote, turned upside down. We all know that every business is a people business.

The Hidden Secret of Debt

Originally published on October 16, 2013

When you’re struggling with debt, it’s all consuming. People are looking to figure it out.

Leaders Are Readers: 4 Reasons to Start Today

Originally published on November 29, 2013

A guest post. Chris Mullen sheds new light on a common buzz phrase. His four reasons really get us going.

Your Software Is Your Brand

Originally published on April 7, 2013

Prediction: this subject becomes one of the most popular of 2015. It’s an early trend, but is just getting bigger: software is your BUSINESS, regardless of industry.

5 Ways I Use Evernote Every Day & a Giveaway

Originally published on October 9, 2013

You want to talk about popular? Evernote is popular. Apparently, so is guest poster Sarah Reinhard.

Integrity is not honesty

Originally published on October 2, 2011

A staple.

Without Passion, Your Efforts Are Doomed

Originally published on September 11, 2013

One of the great archive posts. I’ve had more than a couple people share that this one has really hit their core and helped change their direction. Passion speaks to all of us.

Are You an ‘A’ Player?

Originally published on September 28, 2011

One of my top posts of all time. It was my first to ever go popular. A great title that really resonates with leaders and hiring managers.

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Most Important Lesson of 2014: Brutal Honesty - David DeWolf

My Single Most Important Lesson of 2014: Brutal Honesty

My favorite week of the year is the one that sits between Christmas and New Year’s. It provides natural downtime that I use to spend meaningful time with my family, reflect on the past 12 months, and plan for the upcoming year. During this time, one of my practices is to contemplate what I’ve learned since last year at this time.

This year, the lessons jumps off the page.

Brutal honesty, communicated with charity, is one of the most powerful leadership — and life — tools available.

In his book The 5 Temptations of a CEO, Patrick Lencioni describes 5 deadly temptations that destroy the leadership abilities of any CEO. When I read the book, it hit me squarely in the face: Popularity over accountability; being well liked by those we lead.

Here’s how Patrick summarizes this temptation.

“[It] is one of the most common and it has to do with the dangerous need to be well liked by the people whom we lead. This is problematic because it makes us hesitate when it is time to hold someone accountable for their behavior or their failure to deliver results. Fearing that they will hurt the feelings of their staff members, too many CEOs avoid giving them the feedback they need to improve. This ultimately hurts the organization’s ability to produce results.”

After reading this book in 2013, I decided that 2014 was the year to put it into practice.

Here’s what I found.

Brutal honesty releases stress.

As with so many areas of our lives, issues become larger than life when we don’t deal with them head-on. By addressing issues, we relieve the stress that builds up by not communicating – and often we find that the anticipation was much worse than the conversation itself.

In one example, I spoke to one of my leadership team members about an issue I should have addressed a year prior, but hadn’t. When I confronted the situation, I found that it wasn’t really as big of a deal as I had made it out to be. In fact, my teammate was relieved that I had the courageous conversation and expressed a desire for the same outcome I was after. Simply putting the issue on the table took 90% of the air out of the balloon and things have been steadily improving ever since.

Brutal honesty motivates people.

Most people actually want to improve themselves and many actually thrive off of feedback. By sharing our perspective, we afford those we lead with the opportunity to get better. We encourage change.

The power of blunt feedback sank in for me when I spoke with one of my team members about a personality trait that was holding her back from effective leadership. I had significant angst about the conversation, as it seemed rather personal in nature. Much to my surprise, the individual was grateful for the blunt feedback. She immediately sought out advice and perspective from others and found ways to nip the issue in the bud. In fact, in the six months since, I have not experienced the issue.

Brutal honesty clears the air.

Sometimes, those who need to hear feedback already know the issue. Holding it back only creates stress them as much as it does for you. They wonder what you think, whether they have your support, and what they should do. Putting it out in the open clears the air.

One of my teammates is perceived as someone he’s really not. The perception stems from his past and his personality, but, it’s really an unfair assessment made by people who don’t really know him. But every once in a while he fuels this perception by the way he acts in the moment.

I decided to confront him about it and share what I thought was going on. By doing so, I learned that this perception is one of his biggest pet peeves. He was relieved to know that I had noticed and to be able to talk openly with me about it. He genuinely wanted my advice about the issue, but didn’t want to bring it to my attention. By having the open conversation, I was able to clear the air and we were able to begin got collaborate on the issue to gather.

Brutal honesty clarifies misconceptions.

It’s easy to to misunderstand actions and reactions. When we don’t talk about things that are creating stress, we are probably communicating our discomfort in other ways.

I failed to have a courageous conversation with one of my team members this year. My teammate had agreed to help me out with an initiative that went over and above his core responsibilities and he failed to execute on it. As time dragged on, I felt compelled to fix the problem. The issue became significant enough that I had to take action.

After I fixed the issue myself – something my teammate made note of – we spoke about what had happened. My teammate knew he had failed, and was relieved to hear that I recognized it as well. By stating the obvious and communicating openly, he came to understand that I recognized that this initiative was above and beyond his daily job, but that I was still disappointed in his performance.

This dose of reality was exactly what he needed. Without the conversation, he was left wondering what I really thought. Did I not trust him to do it? Was I furious that he was failing at his job? How did I perceive the situation?

I only wish I would have had the hard conversation before it had boiled over. It would have given him the motivation needed to take care of the issue himself.

Of course, brutal honesty can’t be delivered brutally. It must be delivered in charity. If you truly have — and the other person knows that you truly have — their best interest in mind, most people take feedback really well. By delivering hard feedback, by having the courageous conversation, we create higher performing teams and save ourselves issues down the road.

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Resources to Become a Better Leader - David DeWolf

Resources to Become a Better Leader

What are a few resources you would recommend to someone looking to gain insight into becoming a better leader?

For the past few months, I’ve been asked more often what books and resources I would recommend to other leaders. It’s hard to say, because every leader has their own strengths and weaknesses, their own things that they’re naturally good at and that they need to work on. Every leader has different things that they consume.

By and large, though, if I had to pick one general thing for the masses, I would say that leaders would serve themselves well by reading Patrick Lencioni’s books. His books provide leadership fables that tell very descriptive stories that teach lessons about leadership. These leadership fables typically go back to fundamentals about creating high-performing teams and healthy organizations.

The Five Dysfunctions of a Team describes the importance of building trust, of having true debate and vulnerability within an organization, and of holding each other accountable. These are fundamentals for high-performing teams.

Silos, Politics and Turf Wars describes how a single vision, a single important priority, can galvanize a team and get them to work together.

All of his books teach us how to build teams in an intentional manner, not overlooking those things that some depict as soft but ultimately are the things that truly create a high-performing culture and a differentiated team.

Question: What are your favorite leadership resources? I’d love to hear from you! You can leave a comment by clicking here. Learn to live an integrated life with humble confidence. Get it Now Join the Discussion

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Episode #004: The Power of a Life Plan [Podcast]

This week, we discuss the power of a life plan. I’m joined by cohost Mike Manion, Area President of Convene’s Mid-Atlantic region and a frequent host on various radio shows and podcasts.

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Why is a life plan important?

A life plan integrates every aspect of your life together We’re not living a zero-sum game, though we often act as though we are With a life plan, my life is more complete and integrated

My life is actually more like the Olympic rings. The more you scale the Olympic rings, the more they overlap. It’s at the intersection points, where the circles touch and overlap, that I learned I need to spend more time and planning.

Figuring out what to focus on is a creative process. First, I had to figure out what my circles are. Then, I had to figure out how they intersected.

My circles are God and my faith life, myself, family (as a husband and as a father and in my extended family), and my work. All of them intersect.

It’s hard to set aside time to think, but I chose to prioritize working on my life versus just being in my life and letting it run me. I was able to find creative ways to let every single circle impact every other circle.

The 2-step process for making your life plan

Figure out what the circles in your life are Spend time thinking about how they intersect and overlap so that they can benefit each other

If you can take the time to identify your priorities and find the ways where they can complement and support each other while driving your forward, you’ll be living an integrated life.

Question: My challenge for your: find the time in the next 14 days to set aside two 6-hour blocks to simply think through your life. What are your priorities? Where do the concentric circles overlap? I’d love to hear from you! You can leave a comment by clicking here.


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The Changing Face of the Modern CTO - David DeWolf

The Changing Face of the Modern CTO

A few days ago I published the job description I wrote for the CTO 3Pillar is looking to hire in the next few months. In that post I mentioned the changing face of the CTO.

In the ‘software is your brand’ world, the role of the Chief Technology Officer is just as much about the product as it is about the technology. Modern CTOs are innovators and strategists. They understand revenue models and work closely with user experience designers to build engaging products.

The pocket-protector wearing CTO that spearheads an R&D organization steeped in algorithm development and academic research has few options. The CTO of the future is being called out of the back office and into the C-Suite.

Modern CTOs must excel at collaborating across the business and providing executive leadership. They must maintain their technical expertise, but, business acumen is just as important.

Three organizational models have begun to emerge among product organizations. Each requires a new breed of CTO.

The CTO as Product Executive

Many organizations have come to expect CTOs to fulfill the product executive responsibilities. They are as much, if not more, Chief Product Officer as they are Chief Technology Officer. This model centralizes product ownership with the CTO possessing ultimate authority and responsibility over the product. The modern CTO defines both the what (product management) and the what (technology, engineering and process) of the product.

In this model, the successful CTO must drive both innovation and results. They not only embrace, but act as the chief evangelist for lean startup methodologies, ensuring that the product is not only built, but, the right product. The successful candidate has come to appreciate customer experience as much as they have software craftsmanship.

This type of product leadership is most common with B2B and B2B2C business models.

The CMO as Product Executive

In most B2C organizations, product ownership resides with the Chief Marketing Officer, who oversees both product marketing and product management functions. This model creates a healthy tension between product ownership (the what) and implementation (the how).

In this organizational model, the successful CTO must collaborate closely with the CMO. The individual provides an innovation engine that can be rapidly recalibrated to build the right product as defined by continuous user feedback. The CTO becomes a chief collaborate with the CMO, two roles that have traditionally combined like oil and water, speaking two totally separate languages. The successful candidate has come to appreciate business language as much as the programming language.

This type of product leadership can also be found in organizations that require a deeper level of technical expertise – such as those with deep algorithmic intellectual property or those relying on embedded software and requiring hardware integration.

The Dedicated Product Executive

Finally, many organizations have a dedicated product executive. This is most common in small organizations, where, the CEO is the product visionary, or, in much larger organizations where the product executive leads a business unit that is supported by shared marketing and technology services organizations.

In this organizational model the successful CTO must be also be politically savvy, learning to collaborate with multiple executives and negotiate different priorities and differences of opinion amongst various stakeholders. In large organization especially, the CTO that operates with dedicated product executives is a versatile executive leader that is able to drive the technical organization while collaborating with multiple business owners.

The role of the CTO has changed. No longer can the Chief Technology Officer limit herself to deep technological expertise. Regardless of the organizational model, the CTO must, at the very least, collaborate in a meaningful way in ongoing product development.

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