DLGP

Doctor of Leadership in Global Perspectives: Crafting Ministry in an Interconnected World

The Gift of Disappointing Well

Written by: on February 27, 2025

My favorite definition of “leadership” these days is one from Ronald Heifetz: “disappointing people at a rate they can absorb.”[1] This definition came to mind throughout my reading of A Failure of Nerve, especially as Friedman interacted with the concepts of sabotage, systemic toxicity, and how people and organizations can strongly (negatively!) react simply because a leader takes any action.[2] Friedman’s text was at once encouraging, challenging, and disappointing.

My disappointments were three-fold: First, because our culture seems to be moving even more rapidly in the swift-moving current of anxiety and unreasonableness, of self-advancement, enmeshment, and reactivity; nearly three decades after the book’s first release, Friedman’s voice is still like one calling in the wilderness. Second, how I’ve never been exposed to (or can recall being exposed to) Friedman and his systems perspective even while completing a master’s degree in organizational leadership is beyond me; his work is prescient, practical, and incredibly relevant in our anxious world, and I wish I had been invited into its conversations much earlier. Finally, while Friedman recognizes the whole person and the sense of the spiritual, I don’t know how a leader can self-differentiate in a healthy way without Holy Spirit at work in community with others; in this way, the political, familial, and biological frameworks he uses are helpful but incomplete.

As I mentioned, the work was challenging and encouraging, too (I’m more encouraged and challenged than disappointed, so Friedman is leading me well, at least according to Heifetz). I’m currently navigating all that comes with being 18 months into transition following a 41-year senior leader. In this space, I have daily opportunities to disappoint people; I’m hopeful those disappointments are absorbable, but time will tell. I also hope those disappointments are out of healthy, well-differentiated (and Spirit-dependent) leadership. However, Friedman would remind us that we never fully arrive at self-differentiation, and no doubt those I serve would be able to point out where growth in me would be appreciated.[3] The encouragement here is that the disappointment and frustration found in the systemic responses to change—what Friedman calls “sabotage”—are to be expected; this is what happens when leadership enters the ecosystem.[4] In that way, the disappointments of others or even the turbulence found in seasons like mine are part of the gift and sacred calling of leadership.

Another challenge is the propensity for identifying an “enemy” somewhere to hang our dysfunction on. In the disequilibrating season of transition, it’s easy to point to tertiary reasons for difficulties and focus there, making people or circumstances a shared enemy. It’s convenient to find something easy to blame rather than enduring the “acute, temporarily more painful phase” of journeying out of chronic conditions.[5] I have seen this playing out in my context, and I’m grateful to have categories and context for what is happening. I think if we were to gaze into the underworkings of these things with a spiritual perspective, we would be reminded of the reality of principalities and powers that leverage human systems for dysfunction and destruction.[6]

I am encouraged by the reminder that working harder isn’t nearly as crucial as offering healthy presence and that bringing energy rather than information has great value.[7] It’s also personally challenging as someone who presents as an enneagram five (“fives” are notorious for rationing energy and collecting information). [8]As much as I can see an organization needing transformation, this further reveals the need for my personal engagement as one being transformed to bring a fullness of presence and energy even (or especially!) when it seems dangerous and taxing.

Throughout A Failure of Nerve, there is hope in finding healing where things are broken, though we must recognize that the wounds received and brokenness in community don’t get healed in isolation.[9] Here I am once again reminded of our need for the transforming work of Holy Spirit as we journey in community with others and that leaders can’t take others where they aren’t themselves willing to go. I believe it’s as Holy Spirit transforms us into the likeness of Jesus—who personifies great leadership and avoids the pitfalls of “quick-fix” leadership—that we can live into the vision of well-differentiated leadership that Friedman has, not just emerging to be worn down and worn out, but thriving in a world increasingly desperate for humble, authentic, courageous leadership.[10]

[1] Heifetz, Ronald and Marty Linskey. Leadership on the Line: Staying Alive Through the Dangers of Change. (Boston: Harvard Business Review Press, 2017), 128.

[2] Friedman, Edwin H. A Failure of Nerve: Leadership in the Age of the Quick Fix, 10th Anniversary Revised Edition, Kindle. New York: Church Publishing, 2017.

[3] Friedman, 326.

[4] Friedman, 19, 30.

[5] Friedman, 96.

[6] Cf. John 8:44; John 10:10; 2 Corinthians 4:1-4; Ephesians 6:10-18.

[7] Friedman, 177.

[8] Rohr, Richard and Andreas Ebert. The Enneagram: A Christian Perspective. Redwood City: PublishDrive, 2001.

[9] Friedman, 26.

[10] Friedman, 261.

About the Author

mm

Jeremiah Gómez

I get to be Sarah's husband and Jubilee's and Zechariah's dad. I also get to serve as lead pastor at Trinity Church, a dynamic church in the Midwest where we're diligently seeking to Love God, love others, live sent, and be transformed together in community. I love the privilege of working across differences, championing healing and reconciliation in many forms.

9 responses to “The Gift of Disappointing Well”

  1. Joff Williams says:

    Great writing, Jeremiah. You had me laughing out loud with “disappointing people at a rate they can absorb.” I told my pastor father-in-law and he got a chuckle from it too.

    As you identify as someone who may tend to ration your energy and gather information, how do you practically respond to the demands on your energy that come with the territory for leadership, especially in Friedman’s model? In particular, how do you partner with the Holy Spirit to live abundantly within your wiring as a leader?

    • mm Jeremiah Gómez says:

      Thank you, Joff!

      I have yet to meet a leader “in the thick of it” who doesn’t resonate with the Heifetz quote.

      One of the challenges of it speaks to the great question you ask: If we’re not careful, that perspective can move us to “playing not to lose” more than “playing to win.” If I’m playing not to lose, I get more engaged in energy-rationing and information gathering; I begin to function in a scarcity mindset. I now find that is a prompt for me to see where I’m moving into unhealthy patterns and perspectives and engage in communities of abundance and optimism. Having a community of discernment who will speak the truth in love to me and encourage me is so important. I’ve also learned it’s “okay” for me to need space and time to recharge and refill—but it’s more of resting *to* work instead of resting *from* work, if that makes sense. I see that my experience and wiring are gifts to be leveraged, but as Oswald Sanders would remind us, an unguarded strength is a double weakness.

      More than that, each quarter I look at what the big five or six things are that, as the leader, I have to bring my energy to in order to help myself, my family, my teams, and my organization more into vision/mission fulfillment. Each Sunday night or Monday morning, I prayerfully review that and look to what three things I’ll invest energy in toward those larger needs. Those are some rhythms I’m currently engaging in; I’m sure as seasons change, I’ll need to adapt and adjust.

  2. Rich says:

    I am inspired to start a new Etsy venture selling coffee mugs with your catchphrase, “I have daily opportunities to disappoint people.(TM)” Your insight gives a bit of explanation to Friedman’s observation of sabotage. Like it or not, a strong leader’s decisions are not universally popular. Otherwise, leadership is not really needed.

    You mention enneagram five. I will admit that the simple four box models like Myers-Briggs and DISC turned me away from the subject and I have never given enneagram the time of day. Friedman clearly has no use for “a worldview that focuses on classifications such as the psychological diagnosis of individuals or their ‘personality profiles’.”[1] With both your formal training and your experience, how would you respond to Friedman’s dismissal?

    [1] Friedman, 4.

    • mm Jeremiah Gómez says:

      Rich –

      I’ll be the first to purchase that mug!

      When we’ve been in really, really hard leadership seasons, my teenage daughter has often asked “why?” or offered apologies that things are so. stinking. hard. My response is often, “we don’t need strong leaders when everything is easy.” That may not be the whole picture, but it’s an encouraging reminder for me… as were Friedman’s reminders about sabotage.

      I’m not an enneagram apologist, and I don’t pretend to be an expert in its use, but my response to Friedman’s perspective would be that the Enneagram, when used in community, is a really effective tool for development and transformation. It’s more than a “personality profile,” but a tool for recognizing where we need healing toward something more. It’s the only tool I know of that doesn’t start with “here’s where you’re awesome,” but instead with, “where you feel most exposed/‘found out’” is likely the place you need to move toward greater flourishing, and that flourishing is a gift for the world. In that way, I think it is a helpful tool in become well-differentiated.

  3. mm Jess Bashioum says:

    I appreciate how you painted a picture of Friedman as John the Baptist of Leadership. This analogy breaks down for the same reason you say self- differentiation does, the Holy Spirit is not in the process. I wholeheartedly agree of the essential presence of the Spirit to be at work in self-awareness, identity and connections with others. I resonate with the importance to do the work to get out of chronic painful conditions instead of blaming others. if we do not take responsibility for our part, we cannot grow.

    It sounds like you are doing well as a leader in transition. Your awareness that people will be disappointed at some point and your ability to not let it affect your position and identity is a great strength. It seems the Holy Spirit is the one leading in your situation.

    • mm Jeremiah Gómez says:

      Thanks for your response and kind interaction here, Jess!

      The metaphor is certainly lacking *and* I think it’s safe to say there is a lot of truth in what Friedman has to say–truth that has been either unheard, avoided, or misapplied. That said, doing the work he points to on our own, or for our own well-intentioned but flawed ends, will only reveal our need for the new and living way of the Spirit of Jesus to enliven, enable, and direct us.

  4. Alex Mwaura says:

    Great thoughts Jeremiah. I resonate with Heifetz’s quote. All leaders will disappoint but I think people recognize the fallible nature of man and provide space to correct wrongs. Do you think the authentic act of acknowledging mistakes, failure to a team erodes one’s leadership stature?

    • mm Jeremiah Gómez says:

      Thanks, Alex!

      I don’t know that we can lead authentically without trust. I’ve found that the people around me can tell when I’ve made a mis-step, and not acknowledging it can feel to them either like a lack of awareness (at best) or insincerity, which both erode trust. However, it’s probably worse to make an error, own it, and then not learn from it.

      What I’ve found hopeful is that both Heifetz and Friedman appear to say that the disappointment of others is not the problem; it is to be expected as part of well-differentiated leadership. How we help manage that disappointment, and maybe even leverage it, is where we have a great opportunity to partner in transformation.

      What’s your perspective on whether acknowledging mistakes builds or erodes leadership?

  5. mm Ivan Ostrovsky says:

    Jeremiah, I love that “disappointing people at a rate they can absorb!” lol so good!
    Do you think it is possible for the leaders of today to take this approach of disappointing people? How does it look like in a world of AI and sensitivity?

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