This salad makes a great partner for grilled meats like flank steak or tri-tip, chicken, and pork shoulder steaks.
Preheat the grill to medium-high heat. If you’re using a charcoal grill, let the coals cool a bit, so they are not red hot. Alternatively, you can use a grill pan and grill the chicories in batches at high heat.
While the grill is heating, make the dressing. To start, toast the fennel seeds. Heat a small skillet over medium-high heat. Add the fennel seeds and cook until they start to turn golden and fragrant, about 30 seconds to 1 minute. Transfer the toasted fennel seeds to a mortar and pound the seeds into a very coarse powder.Transfer the chile-fennel paste to a medium bowl. Add the lemon juice and whisk to combine. Allow to macerate for 5–10 minutes at room temperature .
Cut the smaller chicories in half and any larger, tighter headed chicories into quarters. Place on a sheet pan. Brush every surface of the cut chicories with olive oil and season with salt and pepper. Place the chicories, cut side down onto the grill. Grill the greens until they start to char and begin to wilt, about 1–3 minutes for the smaller chicories and 2–4 minutes for the larger ones. Flip and continue to cook until the outer leaves start to turn golden brown, about another 1–2 minutes. For the larger chicories, you’ll have to rotate them three times, cooking them on both cut sides and the outer side.
To assemble the dish, arrange the grilled chicories on a serving platter, pulling the leaves apart slightly. Give the reserved dressing another whisk to re-emulsify it, if you need to, and spoon over the grilled chicories, making sure to get it in all the nooks and crannies of the greens. Finish with a sprinkling of flaky salt and serve warm or at room temperature.
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